Hydrochloric Acid → Urea, N'-(2,4-difluorophenyl)-N-heptyl-N-(5-hydroxypentyl)-

HRID 1109064Notes

Reaction equation

HRID 1109064 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N:23]=[C:24]=[O:25].Cl>C(Cl)Cl>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24](=[O:25])[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5932582,4-Difluorophenyl isocyanateHCID 10352800N-(5-hydroxypentyl) heptylamine

Product 1

HCID 11725825Urea, N'-(2,4-difluorophenyl)-N-heptyl-N-(5-hydroxypentyl)-Yield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part C. To a solution of N-(5-hydroxypentyl) heptylamine (11.65 g, 0.0578 mol) in methylene chloride (75 mL) under a nitrogen atmosphere cooled to 0°, 2,4-difluorophenylisocyanate (8.97 g, 0.0578 mol) was added slowly. The reaction mixture was stirred for 1 hour, poured into 1 N aqueous HCl (200 mL) and was extracted with ethyl acetate (300 mL). The combined organic layer was washed with water, brine, dried over magnesium sulfate and was concentrated to give N'-(2,4-difluorophenyl)-N-heptyl-N-5-hydroxypentylurea as a pale yellow oil (20.0 g, 0.056 mol). 1H NMR (CDCl3) δ 8.03 (m, 1H), 6.88-6.59 (m, 2H), 6.45 (bs, 1H), 3.68 (t, 2H), 3.33(m, 4H), 1.81-1.22(m, 16H), 0.907(t,3H).

Workup

  1. extractionwas extracted with ethyl acetate (300 mL)
  2. washThe combined organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-86bce7f4cbab4b4bb43dd3aef6401858
Source dataset
uspto-grants-1994_06
Patent number
US05318984

Reaction notes

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