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Triethylamine → 1-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-N-[4-(trifluoromethyl)phenyl]-3-pyridazinecarboxamide

HRID 1768943
Notes
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Reaction equation

HRID 1768943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10]([C:20](O)=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=C=O)=[CH:27][CH:26]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10]([C:20]([NH:31][C:28]3[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:34])[F:35])=[CH:26][CH:27]=3)=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 233587531-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-3-pyridazinecarboxylic acid

Product 1

HCID 233587551-(3-Chlorophenyl)-1,4,5,6-tetrahydro-6-phenyl-N-[4-(trifluoromethyl)phenyl]-3-pyridazinecarboxamideYield 49.6%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To 0.70 g (0.0022 mol) of the product obtained in Step B, dissolved in 10 mL toluene, was added 0.625 g (0.0030 mol) α,α,α-trifluoro-p-tolylisocyanate and 0.30 g (0.0029 mol) triethylamine. The reaction mixture was heated at reflux for 18 h, cooled to room temperature and concentrated under reduced pressure. The crude product was triturated with ether to afford 0.50 g of a white solid, mp 183°-184° C. 1H NMR (CDCl3) δ: 1.8-2.4 (m, 3H), 2.9 (d, 1H), 5.25 (bs, 1H), 6.95-7.4 (m, 9H), 7.7 (ABq, 4H), 9.02 (bs, 1H). IR (mineral oil): 3300, 1663 cm-1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was triturated with ether

Sources & evidence

ORD record
ord-b77f39a8e1ff46149d2c4da80a9ccc39
Source dataset
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05380718

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes