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

HRID 67500Notes

Reaction equation

HRID 67500 reaction equation
[Cl: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>[Cl: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

4

Reactant 2

HCID 1088SarcosineHCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 101307386-chloro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

29.1 g (0.14 mol) of 6-chloroisatoic acid anhydride are stirred at 110° C. for 1 hour with 13.12 g (0.14 mol) of sarcosine in 150 ml of dimethyl sulphoxide. The solution obtained is concentrated and the residue is recrystallised from alcohol. There is obtained 6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 237°-238° C.

Workup

  1. customThe solution obtained
  2. concentrationis concentrated
  3. customthe residue is recrystallised from alcohol

Sources & evidence

ORD record
ord-fb3e267e1ad844b3bbd3e75e92a54436
Source dataset
uspto-grants-1982_08
Patent number
US04346033

Reaction notes

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