2-Aminothiophenol → 2-(Chloromethyl)benzothiazole

HRID 1253346Notes

Reaction equation

HRID 1253346 reaction equation
[Cl:1][CH2:2][C:3](OCC)(OCC)OCC.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20]>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[S:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 3059222-Chloro-1,1,1-triethoxyethane

Product 1

HCID 3049782-(Chloromethyl)benzothiazoleYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-1,1,1-triethoxyethane (5.9 g) and 2-aminothiophenol (2.5 g) was heated at 80° C. for 15 minutes. After cooling to room temperature, it was dissovled in methylene chloride (30 ml) and the resulting solution was washed with 3N HCl (10 ml) and then with water (20 ml). The organic portion was evaporated and the residue chromatographed over silica gel to obtain 2-chloromethylbenzothiazole (3.35 g; 90% yield), m.p. 34° C.

Workup

  1. washthe resulting solution was washed with 3N HCl (10 ml)
  2. customThe organic portion was evaporated
  3. customthe residue chromatographed over silica gel

Sources & evidence

ORD record
ord-b50bfa9644894d42945dce4dca34c6ea
Source dataset
uspto-grants-1988_05
Patent number
US04748280

Reaction notes

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