Triethylamine → 4-Nitrophenyl methyl(prop-2-yn-1-yl)carbamate

HRID 1785134Notes

Reaction equation

HRID 1785134 reaction equation
[CH3:1][NH:2][CH2:3][C:4]#[CH:5].C(N(CC)CC)C.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>ClCCl>[CH3:1][N:2]([CH2:3][C:4]#[CH:5])[C:14](=[O:15])[O:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 96160N-methylpropyn-2-ylamine

Product 1

HCID 859129134-Nitrophenyl methyl(prop-2-yn-1-yl)carbamateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Methylpropargylamine (600 mg, 8.70 mmol) and triethylamine (878 mg, 8.68 mmol) in dichloromethane (10 ml) were added dropwise, with ice cooling, to a stirred solution of 4-nitrophenyl chloroformate (1.75 g, 8.68 mmol) in dichloromethane (10 ml). The reaction was stirred at ice temperature for 3 hr. then the resulting solution purified by column chromatography on silica using 25% ethyl acetate in iso-hexane as eluent. Thus was obtained 4-nitrophenyl methyl(prop-2-yn-1-yl)carbamate (1.80 g, 89%) as a colourless oil. Dimethylamine (3.0 ml of a 2.0M solution in THF, 6.0 mmol) and 4-nitrophenyl methyl(prop-2-yn-1-yl)carbamate (600 mg, 2.56 mmol), in dichloromethane (7 ml) were stirred at room temperature for 6 days then the reaction solution purified by chromatography on silica using ethyl acetate as eluent to give N,N,N′-trimethyl-N′-prop-2-yn-1-ylurea (164 mg, 46%) as a colourless oil.

Workup

  1. customthen the resulting solution purified by column chromatography on silica using 25% ethyl acetate in iso-hexane as eluent

Sources & evidence

ORD record
ord-57cfa8b9b39645b091a0818a65886850
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

Loading…