Triethylamine → HCID 13368149, compound

HRID 2412306Notes

Reaction equation

HRID 2412306 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][CH2:13][CH:14]2[CH2:16][C:15]2([Cl:18])[Cl:17])[CH:6]=1)=[O:3].[S:19]1[CH2:23][CH2:22][NH:21][CH2:20]1.C(N(CC)CC)C>C(OCC)C>[S:19]1[CH2:23][CH2:22][N:21]([C:2]([O:4][C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][CH2:13][CH:14]3[CH2:16][C:15]3([Cl:18])[Cl:17])[CH:6]=2)=[O:3])[CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10444ThiazolidineHCID 13368148HCID 13368148, compound

Product 1

HCID 13368149HCID 13368149, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.00 g of 4-chloro-3-[(2,2-dichlorocyclopropyl)methoxy]phenyl chloroformate was dissolved in 20 ml of diethyl ether and, to the solution, there were added 0.32 g of thiazolidine and 0.37 g of triethylamine. The mixture was stirred at 0° to -5° C. for an hour and then washed with water. The ether was distilled off from the ether layer and the oily residue was purified by silica gel column chromatography to give 1.02 g of 4-chloro-3-[(2,2-dichlorocyclopropyl)methoxy]phenyl 3-thiazolidinecarboxylate [Compound (7)], which had the melting point of 74°-79.5° C.

Workup

  1. washwashed with water
  2. distillationThe ether was distilled off from the ether layer
  3. customthe oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-594fbf2c57c04856bc42042066158c8e
Source dataset
uspto-grants-1985_01
Patent number
US04491465

Reaction notes

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