Pyridine → HCID 19786510, compound

HRID 1031244Notes

Reaction equation

HRID 1031244 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[NH:13]2)=[O:11])=[CH:5][CH:4]=1.[C:32](Cl)(Cl)=[O:33].N1C=CC=CC=1>C(Cl)Cl.C1(C)C=CC=CC=1>[O:11]=[C:10]1[N:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[N:13]2[C:32](=[O:33])[N:9]1[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:30])[F:31])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 19786515HCID 19786515, compound

Product 1

HCID 19786510HCID 19786510, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.0 g (4.4 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-phenyl-2,3,4,5-tetrahydro-1H-pyrazole-1-carboxamide (Example 3) in 5 ml of methylene chloride was added 4.2 ml (8 mmole) of 1.9M phosgene in toluene. After stirring for 5 minutes 0.8 g (10 mmole) of pyridine was added. The mixture was stirred for 1 hour and then partitioned between diethyl ether and dilute aqueous hydrochloric acid. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate. Filtration, concentration in vacuo, and chromatography on silica gel using diethyl ether and hexanes gave the title compound, mp 148°-150° C.

Workup

  1. additionwas added
  2. custompartitioned between diethyl ether and dilute aqueous hydrochloric acid
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration, concentration in vacuo, and chromatography on silica gel

Sources & evidence

ORD record
ord-895814cfde704ae7b84e297cdb0e9983
Source dataset
uspto-grants-1992_04
Patent number
US05109014

Reaction notes

Loading…