2-Aminothiophenol → 2-(Chloromethyl)benzothiazole

HRID 1981951Notes

Reaction equation

HRID 1981951 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Cl.[Cl:10][CH2:11][C:12](=N)OC>C(Cl)Cl>[Cl:10][CH2:11][C:12]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 12680765Methyl 2-chloroethanimidate--hydrogen chloride (1/1)

Product 1

HCID 3049782-(Chloromethyl)benzothiazoleYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride [prepared according to procedures described by R. Roger and D. G. Neilson, Chem. Rev., 61, 179 (1961)] (8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water (3X); dried over magnesium sulfate 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 magnesium sulfate
  3. concentrationconcentrated to an oil
  4. distillationThe oil is distilled (120°-135° C. at 0.5 mm Hg)

Sources & evidence

ORD record
ord-76347e4196b34040a62698abaeb3a32d
Source dataset
uspto-grants-1986_06
Patent number
US04594425

Reaction notes

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