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

HRID 374061Notes

Reaction equation

HRID 374061 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 1N 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) δ8.03(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-67bd0bb7ee694c1bbcb26969ee705dcf
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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