2-Chloroethyl isocyanate → 3-Ethyl-2-[O-(2-chloroethylcarbamoyl)-oximino]-4-thiazolidinone

HRID 1659143Notes

Reaction equation

HRID 1659143 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[CH2:6][S:5][C:4]1=[N:9][OH:10])[CH3:2].[Cl:11][CH2:12][CH2:13][N:14]=[C:15]=[O:16]>C(Cl)(Cl)Cl.C(#N)C.C(N(CC)CC)C>[CH2:1]([N:3]1[C:7](=[O:8])[CH2:6][S:5][C:4]1=[N:9][O:10][C:15](=[O:16])[NH:14][CH2:13][CH2:12][Cl:11])[CH3:2]

Participants

6

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 737953003-Ethyl-2-oximino-4-thiazolidinone

Product 1

HCID 544791843-Ethyl-2-[O-(2-chloroethylcarbamoyl)-oximino]-4-thiazolidinone

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 g, 3-ethyl-2-oximino-4-thiazolidinone in 100 ml chloroform, 50 ml acetonitrile, 1.32 g., 2-chloroethylisocyanate and 2 drops of triethyl amine was placed in a pressure bottle and left standing overnight at ambient temperature. Concentration yielded 3.0 g of product. Recrystallized from isopropylether - ethyl acetate, m.p. 99°-102°C.

Workup

  1. waitleft
  2. concentrationConcentration

Sources & evidence

ORD record
ord-1600141bb9f34af684982901b647bc70
Source dataset
uspto-grants-1976_06
Patent number
US03966953

Reaction notes

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