3-(Trifluoromethyl)aniline → N,N'-Di-(m-trifluoromethylphenyl)urea

HRID 1243664Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([N:20]=[C:21]=[O:22])[CH:17]=[CH:18][CH:19]=1>ClCCl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([NH:6][C:21]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:23])[F:24])[CH:15]=2)=[O:22])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(Trifluoromethyl)aniline 10 g (62.1 mmol) was added to 500 ml of anhydrous dichloromethane in a 500 ml round bottomed flask. This stirred solution was cooled to 0° C. using an ice water bath. 3-(Trifluoromethyl)phenyl isocyanate 15 g (80.1 mmol) was added drop-wise over a period of 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred at ambient temperatures for 18 hours. During this time a heavy precipitate was formed. This solid was collected by filtration on a Buchner funnel, and was re-suspended in 250 ml of dichloromethane. After approximately 30 minutes of stirring, the solid was again filtered on a Buchner funnel and then placed under vacuum at 40° C. to dry for a period of 24 hours to give 20 g of a white solid (92.5% yield). 1H NMR (400 MHz DMSO) δ 9.20 (s 2H) 8.04 (s 2H) 7.61 (m 2H) 7.54 (t 2H) 7.34 (m 2H). MS: M+1 found 349.

Workup

temperatureto warm to room temperature
customDuring this time a heavy precipitate was formed
filtrationThis solid was collected by filtration on a Buchner funnel
stirringAfter approximately 30 minutes of stirring
filtrationthe solid was again filtered on a Buchner funnel
customplaced under vacuum at 40° C.
customto dry for a period of 24 hours

Sources & evidence

ORD record: ord-5a4c9e6f412e4cddb89c3ab75bb95dc9
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119120B2

Reaction notes

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