Chloromethyl pivalate → Ticlopidine Hydrochloride

HRID 46675

Reaction equation

HRID 46675 reaction equation
[C:1](OC[Cl:9])(=O)C(C)(C)C.[Cl:10][C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[CH2:13][NH:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1>CS(C)=O>[ClH:9].[Cl:10][C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[CH2:13][N:14]1[CH2:15][CH2:16][C:17]2[S:18][CH:19]=[CH:20][C:21]=2[CH2:1]1

Participants

4

Reactant 2

HCID 87885Chloromethyl pivalateHCID 6454012N-((2-chlorophenyl)methyl)thiophene-3-ethylamine

Product 1

HCID 65335Ticlopidine HydrochlorideYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

66.5 g (0.44 M) chloromethyl pivalate is reacted by heating, for 3 hours, with a solution of 103 g (0.4 M) N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine in 300 ml dimethylsulfoxide, to give the title compound in a yield of 51%.

Sources & evidence

ORD record
ord-e1e3cd2e741d47f5826cb8f92d901749
Source dataset
uspto-grants-1979_11
Patent number
US04174448

Linked notes

Loading…