Benzothiazole → HCID 86690039, compound

HRID 2369334Notes

Reaction equation

HRID 2369334 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1.[Al+3].[Cl-].[Cl-].[Cl-].C[Si]([C:29]#[N:30])(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:12][CH:13]2[C:29]#[N:30])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7222BenzothiazoleHCID 7477p-Anisoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86690039HCID 86690039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methoxybenzoylchloride (7.0 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 14 h at room temperature, the reaction mixture was evaporated to dryness in vacuo and the residue was triturated with ether to give 3-(4-methoxybenzoyl)-2,3-dihydrobenzo[d]thiazole-2-carbonitrile, 8.2 g (70%); mp 122-123° C. (Lit.21 122-123° C.). 1H NMR (DMSO-d6) δ 3.82 (3H, s, MeO), 6.72 (1H, brs, C2-H), 6.84 (1H, s, ArH), 7.01-7.14 (4H, m, 4×ArH), 7.52-7.55 (3H, m, 3×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-a22939cfa8cc473086d41ce9269132a9
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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