Allyl isocyanate → 3-Ethyl-2-[O-(allylcarbamoyl) oximino]-4-thiazolidinone

HRID 1659144Notes

Reaction equation

HRID 1659144 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[CH2:6][S:5][C:4]1=[N:9][OH:10])[CH3:2].[CH2:11]([N:14]=[C:15]=[O:16])[CH:12]=[CH2:13]>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][CH2:11][CH:12]=[CH2:13])[CH3:2]

Participants

6

Reactant 2

HCID 15123Allyl isocyanateHCID 737953003-Ethyl-2-oximino-4-thiazolidinone

Product 1

HCID 541478073-Ethyl-2-[O-(allylcarbamoyl) oximino]-4-thiazolidinoneYield 85.6%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 g of 3-ethyl-2-oximino-4-thiazolidinone in 100 ml chloroform and 50 ml of acetonitrile, 1.04 g allylisocyanate and 2 drops of triethylamine was taken in a pressure bottle and left standing overnight at ambient temperature. Concentration yielded 2.6 g of product, m.p. 103°-104°.

Workup

  1. waitleft
  2. concentrationConcentration

Sources & evidence

ORD record
ord-7a4e222aade048c0bc749d9d63b588c3
Source dataset
uspto-grants-1976_06
Patent number
US03966953

Reaction notes

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