Sarcosine → 3,4-dihydro-4,6-dimethyl-2H-1,4-benzodiazepine-2,5(1H)-dione

HRID 67471

Reaction equation

HRID 67471 reaction equation
[CH3:1][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>[CH3:15][N:14]1[C:8](=[O:9])[C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[NH:12][C:11](=[O:13])[CH2:16]1

Participants

4

Reactant 2

HCID 1088SarcosineHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 217089753,4-dihydro-4,6-dimethyl-2H-1,4-benzodiazepine-2,5(1H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 14.0 g (79 mmol) of 6-methylisatoic acid anhydride, 7.04 g (79 mmol) of sarcosine and 80 ml of dimethyl sulphoxide is stirred at 110° C. for 3 hours. The red coloured solution is evaporated in a high vacuum. The residue is treated with 80 ml of ethanol, the product crystallising out. There is obtained 3,4-dihydro-4,6-dimethyl-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 200°-202° C.

Workup

  1. customThe red coloured solution is evaporated in a high vacuum
  2. additionThe residue is treated with 80 ml of ethanol
  3. customthe product crystallising out

Sources & evidence

ORD record
ord-286c6fc2f25a43d8ba2176baee36fbc1
Source dataset
uspto-grants-1982_08
Patent number
US04346034

Linked notes

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