Hexane → 1-[2-Fluoro-5-(trifluoromethyl)phenyl]-3-(4-iodophenyl)urea

HRID 631768Notes

Reaction equation

[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N:20]=[C:21]=[O:22].CCCCCC>ClCCCl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[NH:20][C:21]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-iodoaniline (438 mg, 2.0 mmol) in 15.0 mL 1,2-dichloroethane at rt was added 2-fluoro-5-(trifluoromethyl)phenyl isocyanate (0.304 mL, 2.1 mmol). After 50 minutes 3 mL hexane was added, the mixture cooled to 0° C., the precipitant filtered and rinsed with 10% EtOAc/hexane to give the title compound as a light purple solid (692 mg, 82%). 1H NMR (DSMO-d6) δ: 9.26 (s, 1H), 8.90 (d, J=2.9 Hz, 1H), 8.59 (dd, J=7.3, 2.3 Hz, 1H), 7.60-7.65 (m, 2H), 7.46-7.54 (m, 1H), 7.36-7.43 (m, 1H), 7.29-7.34 (m, 2H).

Workup

filtrationthe precipitant filtered
washrinsed with 10% EtOAc/hexane

Sources & evidence

ORD record: ord-2fb3166e76934f01b725727bffcfa311
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321721B2

Reaction notes

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