Benzothiazole → HCID 86690036, compound

HRID 2369328Notes

Reaction equation

HRID 2369328 reaction equation
[F: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>[F: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 678794-Fluorobenzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86690036HCID 86690036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzoylchloride (6.5 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-fluorobenzoyl)-2,3-dihydrobenzo[d]thiazole-2-carbonitrile, 9.3 g (82%); mp 150-151° C. 1H NMR (DMSO-d6) δ 6.71 (1H, brs, C2-H), 6.85 (1H, s, ArH), 7.04-7.07 (1H, m, ArH), 7.12-7.16 (1H, m, ArH), 7.38-7.40 (2H, m, 2×ArH), 7.52-7.54 (1H, m, ArH), 7.64-7.67 (2H, m, 2×ArH). Anal. Calcd. for (C15H9FN2OS): C, 63.37; H, 3.19; N, 9.85; S, 11.28. Found: C, 63.02; H, 3.27; N, 9.81; S, 11.31.

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-45f87acaa383404d835e9c8c1ec10bfb
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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