4-Nitrobenzoyl chloride → HCID 22405069, compound

HRID 441223Notes

Reaction equation

HRID 441223 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][C:7](=[O:9])[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1.[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C)C1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:14])[CH2:8][C:7](=[O:9])[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]1[C:22](=[O:23])[C:21]1[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 12206142HCID 12206142, compound

Product 1

HCID 22405069HCID 22405069, compoundYield 10.9%

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4,4-dimethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (1.0 g) in N,N-dimethylaniline (20 ml) was added 4-nitrobenzoyl chloride (0.98 g) at ambient temperature. The mixture was stirred at 150° C. for 9 hours. The resulting mixture was diluted with chloroform and the organic layer was washed successively with 1N hydrochloric acid and saturated aqueous sodium bicarbonate. Drying, filtering and the removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (1% methanol in chloroform) to give 4,4-dimethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (195 mg) as a slightly yellow solid.

Workup

  1. washthe organic layer was washed successively with 1N hydrochloric acid and saturated aqueous sodium bicarbonate
  2. customDrying
  3. filtrationfiltering
  4. customthe removal of solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-63adbadf001a48bd877468f5c414890f
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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