Acetic Acid → 1-[(E)-[4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methylphenyl]methylideneamino]-3-(2,2,2-trifluoroethyl)urea

HRID 241527Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[CH2:13][C:12]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=3)=[N:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:27][NH:28][C:29]([NH:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[O:30].C(O)(=O)C.O>CCO>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[CH2:13][C:12]([C:14]3[CH:21]=[CH:20][C:17](/[CH:18]=[N:27]/[NH:28][C:29]([NH:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[O:30])=[C:16]([CH3:22])[CH:15]=3)=[N:11][CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde (i.e. the product of Step 5, 200 mg), 1-amino-3-(2,2,2-trifluoroethyl)urea (145 mg) and acetic acid (0.1 mL) in EtOH (5 mL) was heated at 70° C. for 4 h. Water was added, the reaction cooled to room temperature and the solid was collected by filtration. Recrystallization from diisopropylether yielded the title compound (198 mg, 73%).

Workup

temperaturethe reaction cooled to room temperature
filtrationthe solid was collected by filtration
customRecrystallization from diisopropylether

Sources & evidence

ORD record: ord-b72aeca1527e4bd9b29b6660eab933cd
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653000B2

Reaction notes

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