Water → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde-4-trifluoroethylsemicarbazone

HRID 1525754Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[F:28][C:29]([F:37])([F:36])[CH2:30][NH:31][C:32](=[O:35])[NH:33][NH2:34].O.CC(OC)(C)C>C(O)C.C(O)(=O)C>[F:28][C:29]([F:37])([F:36])[CH2:30][NH:31][C:32](=[O:35])[NH:33][N:34]=[CH:18][C:17]1[CH:20]=[CH:21][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:23]([F:26])([F:24])[F:25])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:22]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde (72.5 g, 0.18 mol) and 4-trifluoroethyl semicarbazide hydrochloride (39.92 g, 0.21 mol) in ethanol (50 mL) and glacial acetic acid (40 mL) was heated at 70° C. over night. After this, water was added until the clear solution became turbid, then MTBE (10 mL) was added and the mixture was allowed to cool to ambient temperature. The resulting precipitate was filtered and washed with water to obtain the title compound (84.10 g, 86%).

Workup

temperatureto cool to ambient temperature
filtrationThe resulting precipitate was filtered
washwashed with water

Sources & evidence

ORD record: ord-ee3538c240d34ed9a6fe89785de81d1d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085541B2

Reaction notes

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