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

HRID 1785115Notes

Reaction equation

HRID 1785115 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]([NH:7][C:8](=[O:19])OC1C=CC([N+]([O-])=O)=CC=1)[C:5]#[CH:6]>C1COCC1.ClCCl>[CH3:1][N:2]([CH3:3])[C:8]([NH:7][CH2:4][C:5]#[CH:6])=[O:19]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 230891794-Nitrophenyl prop-2-ynylcarbamate

Product 1

HCID 44190381Urea, N,N-dimethyl-N-2-propynyl- (9CI)Yield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (3.0 ml of a 2.0M solution in THF, 6.0 mmol) and 4-nitrophenyl prop-2-yn-1-ylcarbamate (800 mg (80% purity), 2.91 mmol) in dichloromethane (7 ml) were stirred at room temperature for 4 hr. then the reaction solution purified by chromatography on silica using ethyl acetate as eluent to give N,N-dimethyl-N′-prop-2-yn-1-ylurea (289 mg, 79%) as a colourless solid.

Workup

  1. customthen the reaction solution purified by chromatography on silica

Sources & evidence

ORD record
ord-7148a8bdb98f4432be05718119742861
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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