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

HRID 1525754
Notes
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Reaction equation

HRID 1525754 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehydeHCID 86681562HCID 86681562, compound

Product 1

HCID 866815614-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde-4-trifluoroethylsemicarbazone
Yield 86.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

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

  1. temperatureto cool to ambient temperature
  2. filtrationThe resulting precipitate was filtered
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes