Water → 3,4-dihydro-4-methyl-7-(trifluoromethyl)-2H-1,4-benzodiazepine-2,5(1H)-dione

HRID 67487Notes

Reaction equation

HRID 67487 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[C:7]2[C:8]([O:10][C:11](=O)[NH:12][C:6]2=[CH:5][CH:4]=1)=[O:9].[NH:17]([CH2:19]C(O)=O)[CH3:18].O>CS(C)=O>[CH3:18][N:17]1[C:8](=[O:9])[C:7]2[CH:14]=[C:3]([C:2]([F:16])([F:15])[F:1])[CH:4]=[CH:5][C:6]=2[NH:12][C:11](=[O:10])[CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 1088SarcosineHCID 538670346-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 212919793,4-dihydro-4-methyl-7-(trifluoromethyl)-2H-1,4-benzodiazepine-2,5(1H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 5.76 g (24.9 mmol) of 5-(trifluoromethyl)isatoic acid anhydride and 2.44 g (27.4 mmol) of sarcosine in 8 ml of dimethyl sulphoxide is stirred at 110° C. for 4 hours, subsequently poured into 70 ml of water and evaporated to dryness in vacuo. After column chromatography on silica gel using ethyl acetate/n-hexane (9:1) for the elution and recrystallisation of the product from ethanol, there is obtained 3,4-dihydro-4-methyl-7-(trifluoromethyl)-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 203°-206° C.

Workup

  1. customevaporated to dryness in vacuo
  2. washfor the elution and recrystallisation of the product from ethanol

Sources & evidence

ORD record
ord-1ccc7a2fae5547c8b2820a87a280e50b
Source dataset
uspto-grants-1982_08
Patent number
US04346034

Reaction notes

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