Chloroacetonitrile → HCID 9979758, compound

HRID 1587479Notes

Reaction equation

HRID 1587479 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[NH:14][C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:33][C:34]#[N:35]>CN(C)C=O>[C:34]([CH2:33][N:14]1[C:15]2[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=2[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:18][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C:13]1=[O:29])#[N:35]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 2756242Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamate

Product 1

HCID 9979758HCID 9979758, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1,3-Dihydro-3(R,S)-[(benzyloxycarbonyl)amino]-5-phenyl-2H-1,4-benzodiazepin-2-one (1.5 g) was dissolved in 25 ml of dry N,N-dimethylformamide at 0° C. To this solution was added 218 mg of (60%) sodium hydride and the resulting reaction mixture was stirred for 15 minutes. Chloroacetonitrile in 1 ml of dry N,N-dimethylformamide was then added and the reaction mixture was allowed to warm to room temperature. After 1 hour the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and 10% citric acid solution. The organic phase was washed with brine, then dried (sodium sulfate), and concentrated to give a solid. The title compound (1.53 g, 93%) was obtained in pure form after flash silica gel chromatography employing ethyl acetate-hexane (1:2 v/v) as eluant.

Workup

  1. customthe resulting reaction mixture
  2. concentrationAfter 1 hour the reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 10% citric acid solution
  4. washThe organic phase was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customto give a solid

Sources & evidence

ORD record
ord-65562908051b4c8f8823710359019b1b
Source dataset
uspto-grants-1993_06
Patent number
US05218114

Reaction notes

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