2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one → HCID 22405146, compound

HRID 441224Notes

Reaction equation

HRID 441224 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH2:4][CH2:3][C:2]1=[O:12].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23](Cl)(=[O:25])=[O:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23]([N:5]2[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:1][C:2](=[O:12])[CH2:3][CH2:4]2)(=[O:24])=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 2237712,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-oneHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 22405146HCID 22405146, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (700 mg) in pyridine (10 ml) was added 3,4-dimethoxybenzenesulfonyl chloride (1.07 g) and the mixture was stirred at ambient temperature for 2 hours. The resulting mixture was diluted with ethyl acetate, and then the organic solution was washed successively with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine. Drying, filtering and the removal of solvents afforded a crude product. The crude product was triturated with a mixture of diethyl ether and n-hexane (1:1) to give 5-(3,4-dimethoxybenzenesulfonyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (1.33 g) as a yellow powder.

Workup

  1. washthe organic solution was washed successively with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customthe removal of solvents
  5. customafforded a crude product
  6. customThe crude product was triturated with a mixture of diethyl ether and n-hexane (1:1)

Sources & evidence

ORD record
ord-f024a11c1e6b4c4cbc11b4adf77e1f4e
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

Loading…