Acetic Anhydride → HCID 20329320, compound

HRID 261168Notes

Reaction equation

HRID 261168 reaction equation
[OH:1][CH2:2][C:3]1[N:7]2[C:8]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:9]=3[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](=[O:13])[CH2:12][C:6]2=[N:5][N:4]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1.C(Cl)Cl>[C:25]([O:1][CH2:2][C:3]1[N:7]2[C:8]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:9]=3[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](=[O:13])[CH2:12][C:6]2=[N:5][N:4]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 20329310HCID 20329310, compound

Product 1

HCID 20329320HCID 20329320, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3.4 g of 1-(hydroxymethyl)-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,5]benzodiazepin-5-one 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 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-74bf03bc92a446b0871a4350fd3319fb
Source dataset
uspto-grants-1979_08
Patent number
US04164498

Reaction notes

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