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

HRID 2260508Notes

Reaction equation

HRID 2260508 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)-N-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 extracted with ethyl acetate (300 mL). The combined organic extracts were washed with water and brine, then 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) δ8.03 (m, 1H), 6.88-6.59 (m, 2H), 6.45 (bs, 1H), 3.68 (t, 2H, J=8.4 Hz), 3.33 (m, 4H), 1.81-1.22 (m, 16H), 0.91 (t,3H, J=6.7 Hz).

Workup

  1. extractionextracted with ethyl acetate (300 mL)
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-bd9fbdd339924bccaa19d923575a370a
Source dataset
uspto-grants-1995_12
Patent number
US05478830

Reaction notes

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