Sarcosine → 7-Bromo-4-methyl-3,4-dihydro-1H-benzo[E][1,4]diazepine-2,5-dione

HRID 851646Notes

Reaction equation

HRID 851646 reaction equation
[Br: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]>CS(C)=O>[Br: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

4

Reactant 2

HCID 1088SarcosineHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 52976447-Bromo-4-methyl-3,4-dihydro-1H-benzo[E][1,4]diazepine-2,5-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 39.5 g of 5-bromoisatoic acid anhydride, 14.5 g of sarcosine and 150 ml of dimethyl sulphoxide is heated to 100° while stirring. After completion of the gas evolution, the mixture is stirred at 100° for a further 30 minutes and subsequently poured into 900 ml of ice-water. The precipitated crystals are filtered off under suction, washed with water and dried at 50° in vacuo over phosphorus pentoxide. There is obtained 7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione as light beige crystals. A sample recrystallized from methanol has a melting point of 260°-261°.

Workup

  1. temperatureis heated to 100°
  2. stirringAfter completion of the gas evolution, the mixture is stirred at 100° for a further 30 minutes
  3. filtrationThe precipitated crystals are filtered off under suction
  4. washwashed with water
  5. dry with materialdried at 50° in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-278a1bf61e5249dfb610e4e10f235014
Source dataset
uspto-grants-1983_05
Patent number
US04386028

Reaction notes

Loading…