Methyl Isocyanate → HCID 53921615, compound

HRID 1659145Notes

Reaction equation

HRID 1659145 reaction equation
[CH3:1][N:2]([CH3:12])[N:3]1[C:7](=[O:8])[CH:6]([CH3:9])[S:5][C:4]1=[N:10][OH:11].[CH3:13][N:14]=[C:15]=[O:16]>CC(C)=O.C(N(CC)CC)C>[CH3:12][N:2]([CH3:1])[N:3]1[C:7](=[O:8])[CH:6]([CH3:9])[S:5][C:4]1=[N:10][O:11][C:15](=[O:16])[NH:14][CH3:13]

Participants

5

Reactant 2

HCID 12228Methyl Isocyanate2×HCID 713968523-(Dimethylamino)-2-(hydroxyimino)-5-methyl-1,3-thiazolidin-4-one

Product 1

HCID 53921615HCID 53921615, compoundYield 325.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalyst2×HCID 180AcetoneSolvent

Procedure

A solution of 1.18 g of 3-dimethylamino-5-methyl-2-oximino-4-thiazolidinone in 50 ml acetone, 1.0 g methylisocyanate and 2 drops of triethylamine was placed in a pressure bottle and left standing at room temperature. After 20 hours additional 0.75 ml of methylisocyanate and 2 drops of triethylamine were added and left standing for 24 hours. Concentration yielded 5.0 g of crude product. Crystallized from methylene chloride and isopropyl ether, m.p. 110°-113°C.

Workup

  1. waitleft
  2. customstanding at room temperature
  3. waitleft
  4. concentrationConcentration

Sources & evidence

ORD record
ord-0b5341acea2441dd8c3c57e6ff87a41d
Source dataset
uspto-grants-1976_06
Patent number
US03966953

Reaction notes

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