Benzothiazole → HCID 13301274, compound

HRID 2369331Notes

Reaction equation

HRID 2369331 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1.[Al+3].[Cl-].[Cl-].[Cl-].C[Si]([C:28]#[N:29])(C)C>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:11][CH:12]2[C:28]#[N:29])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7222BenzothiazoleHCID 85014-Chlorobenzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13301274HCID 13301274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorobenzoylchloride (7.2 g, 41.0 mmol was added dropwise to a stirring solution of benzothiazole (5.4 g, 40.0 mmol) in dichloromethane (40 mL) under argon atmosphere. A catalytic amount of AlCl3 and trimethylsilylcyanide (4.1 g, 42.0 mmol) were than added into the reaction mixture. After being stirred for 15 h at room temperature, the reaction mixture was evaporated to dryness in vacuo and the residue was triturated with ether to give 3-(4-chlorobenzoyl)-2,3-dihydrobenzo[d]thiazole-2-carbonitrile, 10.1 g (84%); mp 115-117° C. (lit.21 mp 115-118° C.). 1H NMR (DMSO-d6) δ 6.75 (1H, brs, C2-H), 6.85 (1H, s, ArH), 7.05-7.09 (1H, m, ArH), 7.13-7.17 (1H, m, ArH), 7.52-7.54 (1H, m, ArH), 7.58-7.61 (4H, m, 4×ArH).

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-8552e2214deb4077a69167b9241bc74e
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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