Chloroacetyl chloride → 3-alpha-Chloroacetyl-2-[(o-hydroxyphenoxy)methyl]thiazolidine
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[OH:6][C:7]1[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=1[O:9][CH2:10][CH:11]1[NH:15][CH2:14][CH2:13][S:12]1>ClCCCl>[Cl:1][CH2:2][C:3]([N:15]1[CH2:14][CH2:13][S:12][CH:11]1[CH2:10][O:9][C:8]1[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=1[OH:6])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
Chloroacetylchloride (2.5 ml) is added to a stirred solution of 2-[(o-hydroxyphenoxy)methyl]thiazolidine (6 g) in 1,2-dichloroethane (80 ml) and triethilamine (4.3 ml) cooled at -30° C. After the usual work-up 3-αchloroacetyl-2-[(o-hydroxyphenoxy)methyl]thiazolidine (5.7 g, from Et2O, m.p. 89°-91° C.) is obtained. A stirred solution of the latter compound in 1,2-dichloroethane (50 ml) is heated with solid potassium thioacetate (4 g). After 2 hours, the mixture is washed with water to give, after the usual work-up, 3-acetylthio-acetyl-2-[(o-hydroxyphenoxy)methyl]thiazolidine (6.4 g, from EtOH) m.p. 97°-99° C.
Sources & evidence
- ORD record
- ord-875ec38b4dc649b0b73cd7fe2d2a62f1
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04857643
Reaction notes
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