2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol → 2,6-difluoro-N-[[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]carbamoyl]benzamide

HRID 1679954Notes

Reaction equation

[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[OH:14][C:15]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([NH:6][C:7]([NH:28][C:27]1[CH:26]=[CH:25][C:24]([C:15]([OH:14])([C:16]([F:17])([F:18])[F:19])[C:20]([F:21])([F:22])[F:23])=[CH:30][CH:29]=1)=[O:8])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

0.055 mole of 2,6-difluorobenzoyl isocyanate is dripped into 0.05 mole of 4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-aniline in 150 ml of absolute toluene. The temperature rises to 27° C. The mixture is heated for 3 hours at 50° C. and then filtered while hot, and the filter cake is dried under reduced pressure at 50° C. There is obtained 19.5 g (95% of theory) of N-(2,6-difluoro-benzoyl)-N'-[4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-phenyl]-urea; m.p.: 205°-207° C.

Workup

customrises to 27° C
filtrationfiltered while hot, and the filter cake
customis dried under reduced pressure at 50° C

Sources & evidence

ORD record: ord-80cd7b31df4c4ea6837e6a8edc63f36e
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04271171

Reaction notes

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