22291-74-3

Basic information

• Product Name: 2(3H)-Benzothiazolone, 3-(phenylmethyl)-
• CAS NO: 22291-74-3
• Molecular Formula: C14H11NOS
• Molecular Weight: 241.313
• Mol File: 22291-74-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2(3H)-Benzothiazolone, 3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Benzothiazolone, 3-(phenylmethyl)-(22291-74-3)
• EPA Substance Registry System: 2(3H)-Benzothiazolone, 3-(phenylmethyl)-(22291-74-3)

Safety Data

• Hazardous Substances Data: 22291-74-3(Hazardous Substances Data)

Upstream product

• 30015-71-5 4-benzyl-2,3-dihydro-2-methyl-4H-1,4-benzothiazin-3-one 
• 4614-22-6 3-benzylbenzothiazolium bromide 
• 95-16-9 1,3-Benzothiazole 
• 74982-54-0 4-Benzyl-2-methyl-1-oxo-1,4-dihydro-2H-1λ⁴-benzo[1,4]thiazin-3-one 
• 934-34-9 2(3H)-Benzothiazolone 
• 74982-53-9 4-benzyl-2,3-dihydro-2-hydroxy-2-methyl-4H-1,4-benzothiazin-3-one 
• 100-39-0 benzyl bromide 
• 934-34-9 2-hydroxybenzothiazole 
• 100-44-7 benzyl chloride 

Relevant articles and documents

AlCl3-DMF reagent in the friedel-crafts reaction. Application to the synthesis of symmetrical benzophenone derivatives

Synthesis of series of symmetrical benzophenone derivatives by C-alkylation reaction of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone with carbon tetrachloride in presence of AlCl3-DMF reagent is reported.

Synthesis method of benzothiazolone compound

The invention discloses an economical and mild. The method adopts o-iodoaniline, elemental sulfur and DMF as raw materials, so that the yield of a target product of up to 3 hours can be obtained only 90%, and the synthesis strategy is compatible with a wide range of functional groups.

Experimental and theoretical studies on the thermal decomposition of heterocyclic nitrosimines

A series of substituted 2-nitrosiminobenzothiazolines (2) were synthesized by the nitrosation of the corresponding 2-iminobenzothiazolines (6). Thermal decomposition of 2a-f and of the seleno analogue 7 in methanol and of 3-methyl-2-nitrosobenzothiazoline (2a) in acetonitrile, 1,4-dioxane, and cyclohexane followed first-order kinetics. The activation parameters for thermal deazetization of 2a were measured in cyclohexane (ΔH? = 25.3 ± 0.5 kcal/mol, ΔS? = 1.3 ± 1.5 eu) and in methanol (ΔH? = 22.5 ± 0.7 kcal/mol, ΔS? = -12.9 ± 2.1 eu). These results indicate a unimolecular decomposition and are consistent with a proposed stepwise mechanism involving cyclization of the nitrosimine followed by loss of N2. The ground-state conformations of the parent nitrosiminothiazoline (9a) and transition states for rotation around the exocyclic C=N bond, electrocyclic ring closure, and loss of N2 were calculated using ab initio molecular orbital theory at the MP2/6-31G* level. The calculated gas-phase barrier height for the loss of N2 from 9a (25.2 kcal/mol, MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE) compares favorably with the experimental barrier for 2a of 25.3 kcal/mol in cyclohexane. The potential energy surface is unusual; the rotational transition state 9a-rot-ts connects directly to the orthogonal transition state for ring-closure 9aTS. The decoupling of rotational and pseudopericyclic bond-forming transition states is contrasted with the single pericyclic transition state (15TS) for the electrocyclic ring-opening of oxetene (15) to acrolein (16). For comparison, the calculated homolytic strength of the N-NO bond is 40.0 kcal/mol (MP4(SDQ, FC)/6-31G* + ZPE).