Dimethylcarbamoyl Chloride → HCID 15136714, compound

HRID 1614339Notes

Reaction equation

HRID 1614339 reaction equation
[OH:1][CH2:2][C:3]1([CH3:17])[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[NH:5][C:4]1=[O:16].[CH3:18][N:19]([CH3:23])[C:20](Cl)=[O:21]>N1C=CC=CC=1.C(N(CC)CC)C.C(OCC)(=O)C>[CH3:18][N:19]([CH3:23])[C:20]([O:16][C:4]1[C:3]([CH2:2][O:1][C:20](=[O:21])[N:19]([CH3:23])[CH3:18])([CH3:17])[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=1)=[O:21]

Participants

6

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 13627239HCID 13627239, compound

Product 1

HCID 15136714HCID 15136714, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-hydroxymethyl-4-methyl-1-(4-methoxyphenyl)pyrazolidinone [1.2 g] and dimethylcarbamoyl chloride [0.8 mL] were combined in 10 mL pyridine and 3 mL triethylamine. The resulting mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate (50 mL), washed with saturated ammonium chloride solution (30 mL), dried over MgSO4, and evaporated. The resulting crude material was taken up in 20 mL anhydrous methanol and sodium methoxide [0.4 g] was added. The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with methylene chloride (50 mL), washed with saturated ammonium chloride solution (30 mL), dried over MgSO4, and evaporated. This crude oil was dissolved in 10 mL pyridine and 3 mL triethylamine. Dimethylcarbamoyl chloride [0.45 mL] was added and the resulting mixture was stirred at room temperature for 1 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 0.86 g (45%) of pure 3-(N,N-dimethylcarbamoyloxy)-4-(N,N-dimethylcarbamoyloxymethyl)-4-methyl-1-(4-methoxyphenyl)-2-pyrazoline as a light yellow oil. 1H NMR: 7.1 (4H, dd, j=7,2), 3.8 (4H, m), 3.2 (6H, s), 3.1 (6H, s), 2.0 (3H, s), 1.4 (3H, s).

Workup

  1. washwashed with saturated ammonium chloride solution (30 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. additionsodium methoxide [0.4 g] was added
  5. stirringThe mixture was stirred at room temperature for 1 h
  6. additionThe reaction mixture was diluted with methylene chloride (50 mL)
  7. washwashed with saturated ammonium chloride solution (30 mL)
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. dissolutionThis crude oil was dissolved in 10 mL pyridine
  11. additionDimethylcarbamoyl chloride [0.45 mL] was added
  12. stirringthe resulting mixture was stirred at room temperature for 1 h
  13. additionThe reaction mixture was diluted with ethyl acetate (50 mL)
  14. washwashed with saturated ammonium chloride solution (30 mL)
  15. dry with materialdried over MgSO4
  16. customevaporated

Sources & evidence

ORD record
ord-3386cc3c7f0c4cc28513df97f2bf40b5
Source dataset
uspto-grants-1993_03
Patent number
US05196546

Reaction notes

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