Sarcosine → 1H-1,4-Benzodiazepine-2,5-dione, 7-chloro-3,4-dihydro-4-methyl-

HRID 736592Notes

Reaction equation

HRID 736592 reaction equation
[Cl: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>[Cl: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 784805-Chloroisatoic anhydride

Product 1

HCID 98159491H-1,4-Benzodiazepine-2,5-dione, 7-chloro-3,4-dihydro-4-methyl-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-chloroisatoic anhydride 401 (20 g, 101 mmol) and sarcosine (9.02 g, 101 mmol) in DMSO (160 mL) was heated at 150° C. for 5 hr, cooled to room temperature and poured into ice water (750 mL) to furnish a light brown precipitate. This solid was collected by filtration, washed with water (3×200 mL) and dried. The benzodiazepine 402 was obtained as a light brown solid (19 g, 84% yield). This material was used directly in the next experiment.

Workup

  1. temperaturecooled to room temperature
  2. customto furnish a light brown precipitate
  3. filtrationThis solid was collected by filtration
  4. washwashed with water (3×200 mL)
  5. customdried

Sources & evidence

ORD record
ord-c412a53a197c483b8322682cd27316ae
Source dataset
uspto-grants-2009_09
Patent number
US07595395B2

Reaction notes

Loading…