2-Aminothiophenol → 2-(Chloromethyl)benzothiazole
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- washthe resulting solution was washed with 3N HCl (10 ml)
- customThe organic portion was evaporated
- customthe residue chromatographed over silica gel
Sources & evidence
- ORD record
- ord-7628ca281c8a4d939d7e63b118d19a45
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04723010
Reaction notes
Loading…