Triethylamine → 1-(2-Chloroethyl)-3-(1-phenylbut-3-ynyl)urea

HRID 659133Notes

Reaction equation

HRID 659133 reaction equation
[C:1]1([CH:7]([NH2:11])[CH2:8][C:9]#[CH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].C(N(CC)CC)C>ClCCl>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([NH:11][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]#[CH:10])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 12943342HCID 12943342, compound2×

Product 1

HCID 574298141-(2-Chloroethyl)-3-(1-phenylbut-3-ynyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 187 mg of 1-phenylbut-3-yn-1-amine (Formula 17) in 5 mL of dichloromethane was added 0.16 mL of 2-chloroethyl isocyanate and 0.26 mL of triethylamine. The mixture was stirred at room temperature for 2 hours. Then, dichloromethane was removed. Column chromatography (3% methanol/dichloromethane) followed by recrystallization from chloroform to give 25 mg of 1-(2-chloroethyl)-3-(1-phenylbut-3-ynyl)urea (Formula 18) as a white solid and 200 mg of impure material which was used without further purification. 1H NMR (300 MHz, CDCl3) δ 2.02-2.04 (m, 1H), 2.64-2.82 (m, 2H), 3.49-3.61 (m, 4H), 4.80 (br, 1H), 4.92-5.05 (m, 2H), 7.26-7.37 (m, 5H)

Workup

  1. customThen, dichloromethane was removed
  2. customColumn chromatography (3% methanol/dichloromethane) followed by recrystallization from chloroform

Sources & evidence

ORD record
ord-6bb944e4409f4c0cbc995ffc58bfd5ab
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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