4-Acetylaminopyrazole → HCID 20561808, compound

HRID 1155320Notes

Reaction equation

HRID 1155320 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13](Br)[C:12]([NH:17][C:18](=[O:48])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:47])[CH:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]([CH2:40][CH3:41])([CH3:39])[CH3:38])=[CH:33][C:32]=3[C:42]([CH2:45][CH3:46])([CH3:44])[CH3:43])[CH2:28][CH3:29])[CH:20]=2)=[N:11]1.[C:49]([NH:52][C:53]1[CH:54]=[N:55][NH:56][CH:57]=1)(=[O:51])[CH3:50]>C(OCC)(=O)C>[C:49]([NH:52][C:53]1[CH:54]=[N:55][N:56]([CH:13]2[C:14](=[O:15])[N:10]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=3[Cl:9])[N:11]=[C:12]2[NH:17][C:18](=[O:48])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:47])[CH:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]([CH2:40][CH3:41])([CH3:39])[CH3:38])=[CH:33][C:32]=3[C:42]([CH2:45][CH3:46])([CH3:44])[CH3:43])[CH2:28][CH3:29])[CH:20]=2)[CH:57]=1)(=[O:51])[CH3:50]

Participants

4

Reactant 2

HCID 123468944-AcetylaminopyrazoleHCID 20555344HCID 20555344, compound

Product 1

HCID 20561808HCID 20561808, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

17.8 g of 1-(2,4,6-trichlorophenyl)-3-{3-[2-(2,4-di-tert-amylphenoxy)butyramido]benzamido}-4-bromo-5-oxo-2-pyrazoline and 10 g of 4-acetamidopyrazole were well mixed in a mortar and heated at 100° C. for 2 hours. To the reaction mixture, 200 cc of ethyl acetate was added and the mixture was washed several times with water. The ethyl acetate layer was dried with anhydrous sodium sulfate and concentrated. Upon crystallization of the residue from a solvent mixture of acetonitrile and ethyl acetate, 12.1 g of Coupler (1) was obtained. The melting point of the coupler was 135° to 141° C.

Workup

  1. washthe mixture was washed several times with water
  2. dry with materialThe ethyl acetate layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customUpon crystallization of the residue
  5. additionfrom a solvent mixture of acetonitrile and ethyl acetate, 12.1 g of Coupler (1)
  6. customwas obtained
  7. customwas 135° to 141° C.

Sources & evidence

ORD record
ord-e03b12032fce4a3884916c517b2facce
Source dataset
uspto-grants-1981_11
Patent number
US04301235

Reaction notes

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