2,4-Difluorophenyl isocyanate → HCID 10339996, compound

HRID 374074Notes

Reaction equation

[CH2:1]([NH:8][CH2:9][CH2:10][C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]=[C:26]=[O:27]>C(Cl)Cl>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[NH:25][C:26](=[O:27])[N:8]([CH2:9][CH2:10][C:11]([CH3:15])([CH3:16])[CH2:12][CH2:13][OH:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Part C. A solution of the amine prepared in Part C (4.26 g, 18.6 mmol) in methylene chloride (20 mL) was cooled to 0° C., and a solution of 2,4-difluorophenyl isocyanate (2.20 mL, 18.6 mmol) in methylene chloride (20 mL) was added dropwise with stirring over 1 hour. After slow warming to ambient temperature over 18 hours, the reaction mixture was concentrated under vacuum, and the residual oil was purified by flash chromatography to afford N'-(2,4-difluorophenyl)-N-(3,3-dimethyl-5-hydroxypentyl)-N-heptylurea as a colorless oil (2.31 g, 6.01 mmol, 32%). 1H NMR (CDCl3) δ7.93(br q,1H,J=6.2Hz); 6.89-6.78(m,3H); 3.76(t,2H,J=6.3Hz); 3.38-3.24(m,4H); 2.36(br s,1H); 1.65-1.52(m,6H); 1.36-1.24(m,8H); 0.97(s,6H); 0.89(t,3H,J=6.6Hz).

Workup

temperatureAfter slow warming to ambient temperature over 18 hours
concentrationthe reaction mixture was concentrated under vacuum
customthe residual oil was purified by flash chromatography

Sources & evidence

ORD record: ord-9f71fface8224a89959a4d500f1547bf
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166214

Reaction notes

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