Acetic Anhydride → HCID 135829355, compound

HRID 963483Notes

Reaction equation

HRID 963483 reaction equation
[CH:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:18])[CH2:9][N+:8]=2[O-])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]([O:23]C(=O)C)(=[O:22])[CH3:21]>C(Cl)(Cl)Cl>[C:20]([O:23][CH:9]1[N:8]=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:18])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178516818HCID 178516818, compound

Product 1

HCID 135829355HCID 135829355, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 5-cyclohexy-2,3-dihydro-1H-1,4-benzodiazepin-2-one-4-oxide (0.70 g) in chloroform (10 ml) was added acetic anhydride (3.7 ml) at ambient temperature and the mixture was heated for 4 hours at 70° C. After cooling, the mixture was concentrated in vacuo. The residue was taken up with chloroform. The organic layer was washed with saturated aqueous sodium carbonate, dried over magnesium sulfate, filtered off and concentrated in vacuo to give a crude product. The crude product was purified by column chromatography on silica gel with chloroform to give (3RS)-3-acetoxy-5-cyclohexyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. washThe organic layer was washed with saturated aqueous sodium carbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo
  7. customto give a crude product
  8. customThe crude product was purified by column chromatography on silica gel with chloroform

Sources & evidence

ORD record
ord-3709955e13d2435090da73d74c60e87d
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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