Chloroacetyl chloride → HCID 13603691, compound

HRID 1722827Notes

Reaction equation

[Cl:1][CH2:2][C:3](Cl)=[O:4].[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH:15]1[NH:19][CH2:18][CH2:17][S:16]1>ClCCCl.C(N(CC)CC)C>[Cl:1][CH2:2][C:3]([N:19]1[CH2:18][CH2:17][S:16][CH:15]1[CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[O:6][C:3](=[O:4])[CH2:2][Cl:1])=[O:4]

Participants

Conditions

Temperature: -10 °C

Procedure

α-Chloroacetylchloride (13.4 g, 9.5 ml) is added, with exclusion of humidity, under stirring, in 30 minutes, to a solution of the above thiazolidine (12 g) in 1,2-dichloroethane (120 ml) and triethylamine (18 ml), cooled at -10° C. Stirring is continued for 1 hour at 0° C. and the mixture is partitioned with water. The organic phase is separated, washed with water, dried on CaCl2 and the solvents are evaporated to dryness in vacuum. Crystallization from Et2O gives 3-α-chloroacetyl-2-[2'-(o-α-chloroacetoxy-phenyl)ethyl]thiazolidine (12 g), m.p. 88°-89° C. (hexane/AcOEt 7:3, Rf =0.5). A solution of this compound (6 g) in acetone (30 ml) is treated with potassium thioacetate (4.1 g) under stirring for 30 minutes. The mixture is filtered from the inorganic materials, the acetone is evaporated under vacuum and the residue is partitioned between water and EtOAc. From the organic phase after the usual work-up it is obtained 3-acetylthioacetyl-2-[2'-(o-acetylthioacetoxyphenyl)ethyl]thiazolidine as a colourless oil (hexane/AcOEt 7:3, Rf =0.4).

Workup

customthe mixture is partitioned with water
customThe organic phase is separated
washwashed with water
customdried on CaCl2
customthe solvents are evaporated to dryness in vacuum
customCrystallization from Et2O

Sources & evidence

ORD record: ord-a8a881a2a1ed464791547e402fe0eb05
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04857643

Reaction notes

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