Thionyl Chloride → 2-(4-Chloromethyl-benzyl)-benzothiazole

HRID 545597Notes

Reaction equation

HRID 545597 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=1.S(Cl)([Cl:21])=O>C(Cl)Cl>[Cl:21][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67205894(4-Benzothiazol-2-ylmethyl-phenyl)-methanol

Product 1

HCID 672064032-(4-Chloromethyl-benzyl)-benzothiazoleYield 117.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-benzothiazol-2-ylmethyl-phenyl)-methanol (2.1 g, 8.1 mmol) in CH2Cl2 (90 mL) was added thionyl chloride (0.65 mL, 8.9 mmol) and the mixture was stirred at rt for 4 h. The reaction mixture was concentrated to afford the title compound as a tan solid (2.6 g, 100%). MS (ESI): mass calcd. for C15H12ClNS, 273.04; m/z found, 274.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.34 (d, J=8.2 Hz, 1H), 7.89 (d, J=8.2 Hz, 1H), 7.71-7.67 (m, 1H), 7.61-7.58 (m, 1H), 7.50-7.48 (m, 2H), 7.45-7.44 (m, 2H), 4.84 (s, 2H), 4.60 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e541ed4711024538b75f9847d31a4630
Source dataset
uspto-grants-2011_05
Patent number
US07935725B2

Reaction notes

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