Acetic Anhydride → HCID 13809734, compound

HRID 1837465Notes

Reaction equation

HRID 1837465 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4][CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].[C:18](OC(=O)C)(=[O:20])[CH3:19].C(OCC)(=O)C.CO>CC#N>[C:18]([C:4]1[CH:3]=[N:2][NH:1][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 134664BenzodiazepineHCID 21584119Ethylacetate methanol

Product 1

HCID 13809734HCID 13809734, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
18.5 °C

Procedure

To a suspension of benzodiazapine (92.0 g, 0.62 mole) and K2CO3 (90.2 g, 0.65 mole, −325 mesh) in CH3CN (1000 ml) was added acetic anhydride (63.4 g, 58.6 ml, 0.62 mole) in 0.5 h (reaction mixture was cooled in ice water to maintain the reaction mixture temperature between 15-22° C.). The suspension was stirred for 0.5 h at room temperature (check TLC after 30 min, eluent ethyl acetate:MeOH 9:1). The reaction mixture was evaporated and to the residue water (400 ml) was added. The suspension was cooled in ice, filtered, washed with cold water (50 ml×2). Dried under vacuum to give 109.7 g of 4-acetylbenzodiazepine as a white solid, yield 93%).

Workup

  1. customreaction mixture
  2. customThe reaction mixture was evaporated and to the residue water (400 ml)
  3. additionwas added
  4. temperatureThe suspension was cooled in ice
  5. filtrationfiltered
  6. washwashed with cold water (50 ml×2)
  7. customDried under vacuum

Sources & evidence

ORD record
ord-71307433987645e4a36211305070143d
Source dataset
uspto-grants-2004_08
Patent number
US06784172B2

Reaction notes

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