HCID 86734706, compound → HCID 21437150, compound

HRID 2397205Notes

Reaction equation

HRID 2397205 reaction equation
[Br-].[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:4]=1[N:11]1[C:15](=[O:16])[CH:14]([N+:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([NH:23][C:24](=[O:54])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[O:53])[CH:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([CH2:46][CH3:47])([CH3:45])[CH3:44])=[CH:39][C:38]=3[C:48]([CH2:51][CH3:52])([CH3:50])[CH3:49])[CH2:34][CH3:35])[CH:26]=2)=[N:12]1.[H][H]>C(O)(=O)C.[Ni]>[Cl:10][C:5]1[CH:6]=[C:7]([Cl:9])[CH:8]=[C:3]([Cl:2])[C:4]=1[N:11]1[C:15](=[O:16])[CH:14]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:13]([NH:23][C:24](=[O:54])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[O:53])[CH:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([CH2:46][CH3:47])([CH3:45])[CH3:44])=[CH:39][C:38]=3[C:48]([CH2:51][CH3:52])([CH3:50])[CH3:49])[CH2:34][CH3:35])[CH:26]=2)=[N:12]1

Participants

5

Reactant 2

HCID 86734706HCID 86734706, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 21437150HCID 21437150, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

15 Grams of 1-(2,4,6-trichlorophenyl)-3-[3-{α-(2,4-di-tert-amylphenoxy)butyramido}benzamido]-4-(1-pyridinio)-5-oxo-2-pyrazoline bromide (Compound 1-2; m.p: 260° - 262° C.) was dissolved in 300 ml of acetic acid, with 10 g of Raney nickel being added thereto. The resulting mixture was maintained at 80° C. and vigorously stirred for 24 hours in a stream of hydrogen. Then, the reaction product was treated in the same manner as described in Example 1. Upon recrystallizing from a chloroform-ethyl acetateacetonitrile mixed solvent (1:1:10 by volume), 8.5 g of Compound 2-2 having a melting point of 186° - 190° C. was obtained.

Workup

  1. additionadded
  2. additionThen, the reaction product was treated in the same manner
  3. customUpon recrystallizing from a chloroform-ethyl
  4. additionacetateacetonitrile mixed solvent (1:1:10 by volume), 8.5 g of Compound 2-2 having a melting point of 186° - 190° C.
  5. customwas obtained

Sources & evidence

ORD record
ord-27f02b315299493792b9ade75aa35f92
Source dataset
uspto-grants-1977_05
Patent number
US04021428

Reaction notes

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