Acetic Anhydride → HCID 18679315, compound

HRID 1633503Notes

Reaction equation

HRID 1633503 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[CH:12]=1.CCN(CC)CC.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C1COCC1>[C:20]([CH:9]1[NH:8][CH2:7][C:6]2[CH:12]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[NH:11][CH2:10]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218539657-Chloro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine

Product 1

HCID 18679315HCID 18679315, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-chloro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (12.5 mmol) was dissolved in a mixture of THF (100 mL), Et3N (19.1 mmol) and acetic anhydride (12.4 mmol). The reaction mixture was heated under reflux for 18 h, cooled to room temperature and partitioned between H2O and EtOAc. The aqueous phase was extracted again 2× with EtOAc and the combined organic layers were dried over MgSO4, filtered and concentrated to a yellow, oily solid. The crude material was purified by column chromatography on silia eluting with EtOAc to yield 3-acetyl-7-chloro-1,2,3,5-tetrahydro-4H-[1,4]benzodiazepine (2.8 mmol, 22%) as a clear oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 h
  3. custompartitioned between H2O and EtOAc
  4. extractionThe aqueous phase was extracted again 2× with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow, oily solid
  8. customThe crude material was purified by column chromatography on silia
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-5a6415343520435fad93957b43e8418c
Source dataset
uspto-grants-2003_01
Patent number
US06503900B2

Reaction notes

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