Water → HCID 54475735, compound

HRID 2226573Notes

Reaction equation

HRID 2226573 reaction equation
CN1CCOCC1.[CH3:8][N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](Cl)=[O:11].Cl.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([CH:29]([NH:31][C:32](=[O:38])[CH:33]([NH2:37])[CH:34]([CH3:36])[CH3:35])[CH3:30])=[CH:26][C:25]=2[CH:39]=1.O>ClCCl>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([CH:29]([NH:31][C:32](=[O:38])[C@H:33]([CH:34]([CH3:35])[CH3:36])[NH:37][C:10]([N:9]([CH3:8])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:11])[CH3:30])=[CH:26][C:25]=2[CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 18965424HCID 18965424, compound

Product 1

HCID 54475735HCID 54475735, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.34 g of N-methylmorpholine and 0.57 g of N-methyl-N-phenylcarbamoyl chloride were successively added to a solution containing 1.1 g of N-[1-(5-chloro-2-benzofuranyl)ethyl]-2-amino-3-methylbutanamide hydrochloride dissolved in 30 ml of dichloromethane, at -15° C. The mixture was allowed to sit and warm naturally to room temperature and then stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the dichloromethane layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residual crude crystal was purified by column chromatography on silica gel, thus obtaining 1.1 g of the desired product in the form of a white powder.

Workup

  1. washAfter the dichloromethane layer was washed with water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residual crude crystal was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9bae951af64c4193b93b17115774d99b
Source dataset
uspto-grants-1994_09
Patent number
US05348976

Reaction notes

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