Methyl Isocyanate → 3'-Chloro-4'-(N-methylcarbamoyloxy)-5'-nitroacetophenone

HRID 1580529Notes

Reaction equation

HRID 1580529 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[CH3:15][N:16]=[C:17]=[O:18]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[O:8][C:17](=[O:18])[NH:16][CH3:15]

Participants

3

Reactant 2

HCID 12228Methyl IsocyanateHCID 215618781-(3-Chloro-4-hydroxy-5-nitrophenyl)-ethanone

Product 1

HCID 215618963'-Chloro-4'-(N-methylcarbamoyloxy)-5'-nitroacetophenone

Procedure

A mixture of 21.5 grams (0.1 mole) 3'-chloro-4'-hydroxy-5'-nitroacetophenone and 85.0 milliliters (a large excess) of methylisocyanate was refluxed for 5 hours. On cooling, a white crystalline product was formed. The product was filtered (weight 18.0 grams, melting point 115°-118° C.) and was identified by characteristic peaks in the infrared spectrum as 3'-chloro-4'-(N-methylcarbamoyloxy)-5'-nitroacetophenone.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureOn cooling
  3. customa white crystalline product was formed
  4. filtrationThe product was filtered (weight 18.0 grams, melting point 115°-118° C.)

Sources & evidence

ORD record
ord-2d1d34664ce748c9befeff1e2ea8202e
Source dataset
uspto-grants-1976_01
Patent number
US03933472

Reaction notes

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