Dimethylcarbamoyl Chloride → Urea, N,N-dimethyl-N-2-propynyl- (9CI)

HRID 1437808Notes

Reaction equation

HRID 1437808 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[CH2:7]([NH2:10])[C:8]#[CH:9].CN(C1C=CC=CN=1)C>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][N:2]([CH3:6])[C:3]([NH:10][CH2:7][C:8]#[CH:9])=[O:4]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 218852-DimethylaminopyridineHCID 239041Propargylamine

Product 1

HCID 44190381Urea, N,N-dimethyl-N-2-propynyl- (9CI)

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl carbamylchloride (0.84 mL, 9.1 mmol) was added to a stirred solution of propargylamine (0.62 mL, 9.1 mmol) and dimethylaminopyridine (22 mg, 0.18 mmol) in pyridine (5 mL) at room temperature. The resulting suspension was stirred at ambient temperature for approximately 15 h. The reaction mixture was diluted with ethyl acetate and washed successively with 1N HCl and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (i-3), which was used without further purification.

Workup

  1. washwashed successively with 1N HCl and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52bfc46730a14e8685bac33106678b71
Source dataset
uspto-grants-2009_11
Patent number
US07622449B2

Reaction notes

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