Acetyl chloride → HCID 20392230, compound

HRID 1863184Notes

Reaction equation

HRID 1863184 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:19])[CH3:18]>C1C=CC=CC=1>[C:17]([N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:16])[C:4]2=[CH:15][S:14][CH:13]=[C:5]12)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 203922504,9-Dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 20392230HCID 20392230, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 7 g. of 4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 2.7 g. of acetyl chloride in 75 ml. of benzene is heated under reflux with stirring for 3 hours. The reaction mixture is cooled in an ice bath and two crops of brown crystals are collected, washed with benzene, dried and combined. Concentration of the benzene provides a third crop which is combined with the first two crops, heated to boiling in 250 ml. of ethyl acetate and filtered while hot. An equal amount of hexane is added, the mixture is cooled and the solid is collected, washed with hexane and dried, giving the desired product, mp. 197°-199° C.

Workup

  1. additionA mixture of 7 g
  2. temperatureunder reflux
  3. temperatureThe reaction mixture is cooled in an ice bath
  4. customtwo crops of brown crystals are collected
  5. washwashed with benzene
  6. customdried
  7. customConcentration of the benzene provides a third crop which
  8. temperatureheated
  9. filtrationof ethyl acetate and filtered while hot
  10. additionAn equal amount of hexane is added
  11. temperaturethe mixture is cooled
  12. customthe solid is collected
  13. washwashed with hexane
  14. customdried

Sources & evidence

ORD record
ord-a8643db0b18343acb6a33eaee6963743
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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