Dimethyl Sulfoxide → 1-formylmethyl-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441257Notes

Reaction equation

HRID 441257 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([C:25](=[O:48])[C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:47])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)=[CH:28][CH:27]=2)[CH2:17][CH2:16][C:15]1=[O:49].C(N(CC)CC)C>ClCCl>[CH:12]([CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([C:25](=[O:48])[C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:33](=[O:47])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)=[CH:30][CH:31]=2)[CH2:17][CH2:16][C:15]1=[O:49])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22405269HCID 22405269, compound

Product 1

HCID 224052661-formylmethyl-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-oneYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (0.134 ml) in dichloromethane (10 ml) was added dimethyl sulfoxide (0.109 ml) at -78° C. and the mixture was stirred at the same temperature. After 10 minutes, 1-(2-hydroxyethyl) -5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (400 mg) in dichloromethane (10 ml) was added dropwise at -78° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added triethylamine (0.537 ml) and the mixture was allowed to ambient temperature. The solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 1-formylmethyl-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (301 mg) as an unstable oil. The oil was used for next step without further purification.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. customwas allowed to ambient temperature
  3. washThe solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bcb89b0f601a4395b784ee5eabf0942a
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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