Pyridine → Ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetate

HRID 325368Notes

Reaction equation

HRID 325368 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.N1C=CC=CC=1.[CH2:19]([S:22](Cl)(=[O:24])=[O:23])[CH2:20][CH3:21]>C(Cl)Cl>[CH2:19]([S:22]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)(=[O:24])=[O:23])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 662791-Propanesulfonyl chlorideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 178470764HCID 178470764, compound

Product 1

HCID 20254391Ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (40 g.) and pyridine (200 ml.) was stirred in a stream of nitrogen gas at 40° C., and to the mixture was dropwise added a mixture of propanesulfonyl chloride (61.3 g.) and methylene chloride (100 ml.) over 2 hours, and then the mixture was stirred for 2 hours at the same temperature. After the reaction, pyridine and methylene chloride were distilled off from the reaction mixture. The residue was dissolved in ethyl acetate, and the solution was washed with water, 1/2 N hydrochloric acid and water in turn and then dried. The ethyl acetate was distilled off from the solution, and the residue was washed with a mixture of ethyl acetate and diethyl ether and then dried to give ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (16.4 g.), mp 140° to 142° C.

Workup

  1. additionto the mixture was dropwise added
  2. stirringthe mixture was stirred for 2 hours at the same temperature
  3. distillationwere distilled off from the reaction mixture
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water, 1/2 N hydrochloric acid and water in turn
  6. customdried
  7. distillationThe ethyl acetate was distilled off from the solution
  8. washthe residue was washed with a mixture of ethyl acetate and diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-8eed00c8b03244d29f2a2a3de7b28e6f
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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