Dimethylcarbamoyl Chloride → HCID 15136699, compound

HRID 1614338Notes

Reaction equation

HRID 1614338 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[C:10](=[O:15])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>N1C=CC=CC=1.C(N(CC)CC)C.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:12][C:11]([CH3:13])([CH3:14])[C:10]([O:15][C:18](=[O:19])[N:17]([CH3:21])[CH3:16])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 15136695HCID 15136695, compound

Product 1

HCID 15136699HCID 15136699, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-4,4-dimethyl-3-pyrazolidinone [1.2 g] and dimethylcarbamoyl chloride [0.56 mL] were combined in 4 mL pyridine and 1.5 mL triethylamine. The resulting mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (50 mL), washed with saturated ammonium chloride solution (30 mL), dried over MgSO4, and evaporated. Chromatography on silica gel gave 0.6 g (37%) of pure 1-benzyl-4,4-dimethyl-3-(N,N-dimethylcarbamoyloxy)-2-pyrazoline as a light yellow oil. 1H NMR: 7.6-7.2 (5H, m), 3.8-3.4 (4H, m), 3.2 (6H, s), 1.2 (6H, s).

Workup

  1. washwashed with saturated ammonium chloride solution (30 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-51b2cad17aae425c8386eb720f8f597f
Source dataset
uspto-grants-1993_03
Patent number
US05196546

Reaction notes

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