Propionyl chloride → 4,9-Dihydro-9-methyl-4-propionyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1863176Notes

Reaction equation

HRID 1863176 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2=[CH:13][S:14][CH:15]=[C:4]2[C:3]1=[O:16].[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>C1C=CC=CC=1>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:17](=[O:20])[CH2:18][CH3:19])[C:5]2=[CH:13][S:14][CH:15]=[C:4]2[C:3]1=[O:16]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 203922504,9-Dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 203922574,9-Dihydro-9-methyl-4-propionyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A reaction mixture comprising 7 g. of 4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one, 3.1 g. (2.9 ml.) of propionyl chloride and 70 ml. of benzene is refluxed for 3 hours and then allowed to stand for 48 hours. The benzene is distilled off. The residue is filtered, washed with ether and dried. The solid is heated to boiling in 300 ml. of ethyl acetate, filtered and the filtrate is chilled. The crystals are collected, washed with ether and dried giving the desired product, mp. 202°-203° C.

Workup

  1. distillationThe benzene is distilled off
  2. filtrationThe residue is filtered
  3. washwashed with ether
  4. customdried
  5. temperatureThe solid is heated
  6. filtrationof ethyl acetate, filtered
  7. temperaturethe filtrate is chilled
  8. customThe crystals are collected
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-5afbed81574d465ab19667f1f6712999
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

Loading…