Methyl Isocyanate → 3-Isopropyl-2-[O-(methylcarbamoyl) oximino]-4-thiazolidinone

HRID 1659140Notes

Reaction equation

HRID 1659140 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[CH2:7][S:6][C:5]1=[N:10][OH:11])([CH3:3])[CH3:2].[CH3:12][N:13]=[C:14]=[O:15]>CC(C)=O.C(#N)C.C(N(CC)CC)C>[CH:1]([N:4]1[C:8](=[O:9])[CH2:7][S:6][C:5]1=[N:10][O:11][C:14](=[O:15])[NH:13][CH3:12])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 713968552-(Hydroxyimino)-3-(propan-2-yl)-1,3-thiazolidin-4-one

Product 1

HCID 867336383-Isopropyl-2-[O-(methylcarbamoyl) oximino]-4-thiazolidinone

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 21918305Acetone acetonitrileSolvent

Procedure

To a solution of 1.0 g of 3-isopropyl-2-oximino-4-thiazolidinone in 50 ml acetone-acetonitrile solution (1:1) was added 1 ml of methylisocyanate and 5 drops of triethylamine. The reaction mixture was placed in a pressure bottle and left overnight at ambient temperature. After concentrating under vacuo the residual oil was diluted with diethylether. On cooling the product crystallized. Recrystallized from ethyl ether. Weight 1.8 g. m.p. 94°-96°C.

Workup

  1. concentrationAfter concentrating under vacuo the residual oil
  2. additionwas diluted with diethylether
  3. temperatureOn cooling the product
  4. customcrystallized
  5. customRecrystallized from ethyl ether

Sources & evidence

ORD record
ord-a617895ddbfa447f9667cda27f19deeb
Source dataset
uspto-grants-1976_06
Patent number
US03966953

Reaction notes

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