HCID 20561806, compound → HCID 20561800, compound

HRID 1155321Notes

Reaction equation

HRID 1155321 reaction equation
Br[CH:2]1[C:6](=[O:7])[N:5]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[N:4]=[C:3]1[NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:19].[CH3:39][C:40]1[C:44]([N+:45]([O-:47])=[O:46])=[CH:43][NH:42][N:41]=1>C(OCC)(=O)C>[Cl:16][C:9]1[CH:10]=[C:11]([Cl:15])[CH:12]=[C:13]([Cl:14])[C:8]=1[N:5]1[C:6](=[O:7])[CH:2]([N:42]2[CH:43]=[C:44]([N+:45]([O-:47])=[O:46])[C:40]([CH3:39])=[N:41]2)[C:3]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:19])=[N:4]1

Participants

4

Reactant 2

HCID 20561806HCID 20561806, compoundHCID 178434564HCID 178434564, compound

Product 1

HCID 20561800HCID 20561800, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

13 g of 4-bromo-1-(2,4,6-trichlorophenyl)-3-(3-octadecylureido)-2-pyrazolin-5-one and 10 g of 3-methyl-4-nitropyrazole were mixed at 90° C. for 2 hours. To the reaction mixture, 200 ml 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. The residual oil was dissolved in 50 ml of chloroform and purified with column chromatography using 500 g of silica gel (art 7734 manufactured by MERCK & Co.) wetted with chloroform as a bulking agent. Upon elution with a solvent mixture of chloroform and ethyl acetate (10:1), 10.9 g of an oily comprising the desired coupler was obtained.

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. dissolutionThe residual oil was dissolved in 50 ml of chloroform
  5. custompurified with column chromatography
  6. washUpon elution
  7. additionwith a solvent mixture of chloroform and ethyl acetate (10:1), 10.9 g of an oily comprising the desired coupler
  8. customwas obtained

Sources & evidence

ORD record
ord-87ed6c802e4c4500ad186e4c7057f95e
Source dataset
uspto-grants-1981_11
Patent number
US04301235

Reaction notes

Loading…