Triethylamine → 5-Fluoro-1-methylcarbamoylisatin

HRID 34552

Reaction equation

HRID 34552 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].C(N(CC)CC)C.[CH3:20][N:21]=[C:22]=[O:23]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:22](=[O:23])[NH:21][CH3:20])[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 2365665-Fluoroisatin

Product 1

HCID 142299485-Fluoro-1-methylcarbamoylisatinYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoroisatin (9.9 g), triethylamine (1 ml) and dimethylformamide (30 ml) is stirred under ice-cooling, and thereto is added dropwise methyl isocyanate (3 g) at the same temperature. The mixture is stirred at room temperature for 30 minutes, and the precipitates are taken by filtration to give 5-fluoro-1-methylcarbamoylisatin (8.7 g). M.p. 230°-232° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 30 minutes
  3. filtrationthe precipitates are taken by filtration

Sources & evidence

ORD record
ord-c25576f7a14c4b82ae9916dfb75fb8cd
Source dataset
uspto-grants-1988_08
Patent number
US04762839

Linked notes

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