Acetic Anhydride → HCID 21701299, compound

HRID 1596346Notes

Reaction equation

HRID 1596346 reaction equation
[CH2:1]([C:3]1[C:13]2[NH:12][C:11](=[O:14])[CH2:10][N+:9]([O-])=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:2].[C:23]([O:26]C(=O)C)(=[O:25])[CH3:24]>C(Cl)(Cl)Cl>[C:23]([O:26][CH:10]1[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:1][CH3:2])[C:13]=2[NH:12][C:11]1=[O:14])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178435662HCID 178435662, compound

Product 1

HCID 21701299HCID 21701299, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 9-ethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one-4-oxide (9.0 g) and acetic anhydride (32 ml) in chloroform (32 ml) was stirred at room temperature overnight. The reaction mixture was evaporated to remove chloroform. Diisopropyl ether was added to the residue to afford powder, which was collected by filtration and washed with diisopropyl ether to give (3RS)-3-acetoxy-5-(2-fluorophenyl)-9-ethyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (6.30 g, 61.3%).

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove chloroform
  3. additionDiisopropyl ether was added to the residue
  4. customto afford powder, which
  5. filtrationwas collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-bcf506310c564cd08addac49dca81d1a
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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