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

HRID 232545Notes

Reaction equation

HRID 232545 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

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 1140TolueneSolvent

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.

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-e561da762aec495e806e5f7457c06f74
Source dataset
uspto-grants-1997_01
Patent number
US05591729

Reaction notes

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