2-Aminothiophenol → 2-(Chloromethyl)benzothiazole

HRID 2119047Notes

Reaction equation

HRID 2119047 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Cl:9][CH2:10][C:11](=N)OC>C(Cl)Cl>[Cl:9][CH2:10][C:11]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 12680764O-methyl 2-chloroacetimidate

Product 1

HCID 3049782-(Chloromethyl)benzothiazoleYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride1 (8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water (3X); dried over MgSO4 and concentrated to an oil. The oil is distilled (120°-135° C. at 0.5 mm Hg) to give 7.8 g (71% yield) of product.

Workup

  1. washThe mixture is washed with water (3X)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to an oil
  4. distillationThe oil is distilled (120°-135° C. at 0.5 mm Hg)

Sources & evidence

ORD record
ord-40fab8ca6da14a068ec34845f53f55c7
Source dataset
uspto-grants-1987_07
Patent number
US04681940

Reaction notes

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