Dimethylcarbamoyl Chloride → HCID 178484671, compound

HRID 2083875Notes

Reaction equation

HRID 2083875 reaction equation
[C:1]1([CH:7]([O:14][C:15](=[O:31])[C:16]([OH:30])=[CH:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37].[Cl-].[NH4+]>C1COCC1>[C:1]1([CH:7]([O:14][C:15](=[O:31])[C:16]([OH:30])=[CH:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=3)[N:22]([C:36](=[O:37])[N:35]([CH3:39])[CH3:34])[CH:21]=2)=[O:19])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178525030HCID 178525030, compound

Product 1

HCID 178484671HCID 178484671, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.432 g (1 mmol) of diphenylmethyl ester obtained in Example 91 in THF (5 ml) was added under ice-cooling, 88 mg (2.2 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 30 minutes at room temperature. Subsequently, to the mixture was added 110 μl (1.2 mmol) of dimethylcarbamoyl chloride under ice-cooling and stirred for 1 hour at room temperature. The reaction mixture was poured into aqueous ammonium chloride and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was removed and the residue was crystallized from ether. The crystal was collected by filtration and washed with ether to give 0.39 g of the titled compound. Yield: 77%.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred for 1 hour at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customThe solvent was removed
  8. customthe residue was crystallized from ether
  9. filtrationThe crystal was collected by filtration
  10. washwashed with ether

Sources & evidence

ORD record
ord-3c2db50c6e5b45c1abe8624d344f1deb
Source dataset
uspto-grants-2004_04
Patent number
US06716605B2

Reaction notes

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