Water → 3,4-Dihydro-7-fluoro-4-methyl-1H-1,4-benzodiazepine-2,5-dione

HRID 67539

Reaction equation

HRID 67539 reaction equation
[F:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[NH:14]([CH2:16]C(O)=O)[CH3:15].O>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:9])[CH2:15][N:14]([CH3:16])[C:7](=[O:8])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1088SarcosineHCID 2885605-Fluoroisatoic anhydride

Product 1

HCID 6589903,4-Dihydro-7-fluoro-4-methyl-1H-1,4-benzodiazepine-2,5-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

24 g (132.5 mmol) of 5-fluoroisatoic acid anhydride are dissolved in 140 ml of dimethyl sulphoxide and treated with 11.8 g (132.5 mmol) of sarcosine. The solution is stirred at 100° C. until the gas evolution ceases (duration: ca 1.5 hours) and subsequently poured into ca 1.2 liters of water. After stirring for 10 minutes, a solid crystallises out. The crystals are filtered off under suction, washed with 1 liter of water and dried. There is obtained 7-fluoro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 262°-263° C.

Workup

  1. stirringAfter stirring for 10 minutes
  2. customa solid crystallises out
  3. filtrationThe crystals are filtered off under suction
  4. washwashed with 1 liter of water
  5. customdried

Sources & evidence

ORD record
ord-6112027367914c058dc503fbbefa51b7
Source dataset
uspto-grants-1982_08
Patent number
US04346035

Linked notes

Loading…