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

HRID 1936546Notes

Reaction equation

HRID 1936546 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]>CC1C=CC(C)=CC=1>[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 7809P-XyleneSolvent

Procedure

25.0 g 6-chloro-isatoic anhydride (II) and 12.4 g sarcosine were suspended under stirring and argon atmosphere in 100 ml p-xylene and heated at reflux for two hours. The suspension was cooled to room temperature and further stirred 1 hour, then filtered off. The precipitate was washed with 25 ml p-xylene twice and dried at 50° C. under vacuum. The solid so obtained (6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione (III)) was digested in 75 ml deionized water at 0° C. for 1 hour, filtered off, washed with 25 ml deionized water and dried under vacuum 18 hours at 80° C. Crude product: 25.2 g as a beige powder. m.p. 230-232° C.

Workup

  1. temperatureat reflux for two hours
  2. filtrationfiltered off
  3. washThe precipitate was washed with 25 ml p-xylene twice
  4. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-5ab8b733aa7240fc8b77795a6849202b
Source dataset
uspto-grants-2002_05
Patent number
US06391873B1

Reaction notes

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