Benzenamine, 2-chloro-5-(trifluoromethyl)- → HCID 19758719, compound

HRID 1586638Notes

Reaction equation

C(O[C:4]([CH2:6][C:7]([O:9][C:10]1[CH:31]=[CH:30][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:12][CH:11]=1)=[O:8])=[O:5])C.[NH2:32][C:33]1[CH:34]=[C:35]([C:40]([F:43])([F:42])[F:41])[CH:36]=[CH:37][C:38]=1[Cl:39]>C1(C)C(C)=CC=CC=1>[Cl:39][C:38]1[CH:37]=[CH:36][C:35]([C:40]([F:42])([F:43])[F:41])=[CH:34][C:33]=1[NH:32][C:4]([CH2:6][C:7]([O:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=1)=[O:8])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of the product from (c) (47 g, 0.112 mol) and 3-amino-4-chlorobenzotrifluoride (21.9 g, 0.112 mol) in xylene (450 ml) were heated to reflux for 5 h. Over the final hour, the volume of the mixture was reduced to 200 ml by distillation. After cooling to about 80° C., the solution was poured into petrol (b.p. 60°-80° C. (1 liter) with rapid stirring. A pale yellow solid was collected by filtration and then recrystallized from petrol (b.p. 60°-80° C.) to give an off white solid (40.5 g, 63%).

Workup

temperatureto reflux for 5 h
distillationOver the final hour, the volume of the mixture was reduced to 200 ml by distillation
additionthe solution was poured into petrol (b.p. 60°-80° C. (1 liter) with rapid stirring
filtrationA pale yellow solid was collected by filtration
customrecrystallized from petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record: ord-748211d894d0421fba9d3e0d5c41bb98
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215878

Reaction notes

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