Acetyl chloride → HCID 60165810, compound

HRID 2369325Notes

Reaction equation

HRID 2369325 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[S:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.[Al+3].[Cl-].[Cl-].[Cl-].C[Si]([C:22]#[N:23])(C)C>ClCCl>[C:1]([N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:5][CH:6]1[C:22]#[N:23])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 7222BenzothiazoleHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 60165810HCID 60165810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetylchloride (4.00 g, 51.0 mmol) was added dropwise to a stirring solution of benzothiazole (6.75 g, 50.0 mmol) in dichloromethane (40 mL) under argon atmosphere. A catalytic amount of AlCl3 and trimethylsilylcyanide (5.1 g, 52.0 mmol) were than added into the reaction mixture. After being stirred for 17 h at room temperature, the reaction mixture was evaporated to dryness in vacuo and the residue was triturated with ether to give 3-acetyl-2,3-dihydrobenzo[d]thiazole-2-carbonitrile, 8.2 g (80%); mp 92-93° C. 1H NMR (DMSO-d6) δ 2.39 (3H, s, Me), 7.05 (1H, s, ArH), 7.16-7.26 (2H, m, 2×ArH), 7.49-7.51 (1H, m, ArH), 7.65 (1H, brs, C2-H). Anal. Calcd. for (C10H8N2OS): C, 58.80; H, 3.95; N, 13.72; S, 15.70. Found: C, 58.85; H, 3.95; N, 13.78; S, 15.76.

Workup

  1. additionthan added into the reaction mixture
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-52f3767442b8441aac175a1315635801
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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