Triethylamine → HCID 57429815, compound

HRID 659137Notes

Reaction equation

HRID 659137 reaction equation
[CH3:1][CH:2]([CH3:7])[CH:3]([NH2:6])[C:4]#[CH:5].[Cl:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13].C(N(CC)CC)C>ClCCl>[Cl:8][CH2:9][CH2:10][NH:11][C:12]([NH:6][CH:3]([CH:2]([CH3:7])[CH3:1])[C:4]#[CH:5])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 14919832HCID 14919832, compound2×

Product 1

HCID 57429815HCID 57429815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 256 mg of 4-methylpent-1-yn-3-amine (Formula 23) in 10 mL of dichloromethane was added 0.5 mL of 2-chloroethyl isocyanate and 0.5 mL of triethylamine. After the mixture was stirred at room temperature for 2 hours, the solvent was removed and column chromatography (40% ethyl acetate/hexane) gave 210 mg of 1-(2-Chloroethyl)-3-(4-methylpent-1-yn-3-yl)urea (Formula 24) as a white solid. 1H NMR (300 MHz, CDCl3) δ 0.95-1.01 (m, 6H), 1.84-1.93 (m, 1H), 2.25-2.26 (m, 1H), 3.51-3.63 (m, 4H), 4.40-4.45 (m, 1H).

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-85d9ab91e82c4e78a844812947fbb74b
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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