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

HRID 486083Notes

Reaction equation

HRID 486083 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 was extracted with ethyl acetate (300 mL). The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and 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=6.7 Hz).

Workup

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

Sources & evidence

ORD record
ord-98994deae8464be090787872c4e331c1
Source dataset
uspto-grants-1994_03
Patent number
US05290801

Reaction notes

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