Triethylamine → HCID 57429817, compound

HRID 659140Notes

Reaction equation

HRID 659140 reaction equation
[C:1]1([CH:7]([NH2:10])[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][CH2:12][CH2:13][N:14]=[C:15]=[O:16].C(N(CC)CC)C>C(Cl)Cl>[Cl:11][CH2:12][CH2:13][NH:14][C:15]([NH:10][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[CH:9])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 11672675HCID 11672675, compound2×

Product 1

HCID 57429817HCID 57429817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 180 mg of 1-phenyl-prop-2-ynylamine (Formula 28) in 5 mL of CH2Cl2 were added 0.1 mL of 2-chloroethyl isocyanate and 0.2 mL of triethylamine. After the mixture was stirred at room temperature for 2 hours, the solvent was removed. Column chromatography (50% ethyl acetate/hexane) gave 153 mg of 1-(2-chloro-ethyl)-3-(1-phenyl-prop-2-ynyl)-urea (Formula 29) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.46 (m, 1H), 3.45-3.49 (m, 2H), 3.52-3.54 (m, 2H), 5.40-5.41 (m, 1H), 5.55-5.57 (m, 1H), 5.74-5.76 (m, 1H), 7.27-7.35 (m, 3H), 7.48-7.50 (m, 2H).

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-4d657d152d774b689ba14ff124c20018
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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