Acetic Anhydride → HCID 20373044, compound

HRID 258545Notes

Reaction equation

HRID 258545 reaction equation
[OH:1][C:2]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]2[C:21](=[O:24])[N:22]=[N:23][C:3]=12.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1.C(Cl)Cl>[C:25]([O:1][C:2]1[C:8](=[O:9])[N:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]2[C:21](=[O:24])[N:22]=[N:23][C:3]=12)(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178518872HCID 178518872, compound

Product 1

HCID 20373044HCID 20373044, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3.4 g of 4-hydroxy-8-chloro-6-phenyl-1H-s-triazolo[4,3-a] [1,5]benzodiazepine-1,5-dione and 1.0 g of acetic anhydride in 10 ml of pyridine are warmed in a steam bath for 0.2 hour and stirred at room temperature for 10 hours. The reaction mixture is cooled, diluted with 100 ml of methylene chloride and washed with 100 ml water containing 0.84 g sodium bicarbonate. The organic phase is washed four times with water, dried and evaporated. The residue is triturated with a minimum amount of ether and the title compound filtered off, dried and recrystallized from methylene chloride and ether.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed with 100 ml water containing 0.84 g sodium bicarbonate
  3. washThe organic phase is washed four times with water
  4. customdried
  5. customevaporated
  6. customThe residue is triturated with a minimum amount of ether
  7. filtrationthe title compound filtered off
  8. customdried
  9. customrecrystallized from methylene chloride and ether

Sources & evidence

ORD record
ord-12fa655584d749cea8d36419c69a7e57
Source dataset
uspto-grants-1977_07
Patent number
US04033947

Reaction notes

Loading…