Dimethyl Sulfoxide → 6-Fluoro-4-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

HRID 67402

Reaction equation

HRID 67402 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])O[C:8](=[O:9])[C:7]=12.[NH:14]([CH2:16]C(O)=O)[CH3:15].CS(C)=O>O>[F:1][C:2]1[C:7]2[C:8](=[O:9])[N:14]([CH3:16])[CH2:15][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1088SarcosineHCID 27830576-Fluoroisatoic anhydride

Product 1

HCID 229145476-Fluoro-4-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

7.2 g (0.04 mol) of 6-fluoroisatoic acid anhydride and 3.9 g (0.044 mol) of sarcosine are added to 10 ml of dimethyl sulphoxide and the mixture is heated at 100° C. for 30 minutes. After cooling and diluting with 15 ml of water, the separated substance is filtered off. After drying, there is obtained 6-fluoro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 214°-217° C. (decomposition).

Workup

  1. temperatureAfter cooling
  2. filtrationthe separated substance is filtered off
  3. customAfter drying

Sources & evidence

ORD record
ord-ed109a50c6c74785aa0911eec8671bdd
Source dataset
uspto-grants-1982_08
Patent number
US04346032

Linked notes

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