Imidazole → HCID 20555349, compound

HRID 1733386Notes

Reaction equation

HRID 1733386 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:39])[CH:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH2:32][CH3:33])([CH3:31])[CH3:30])=[CH:25][C:24]=2[C:34]([CH2:37][CH3:38])([CH3:36])[CH3:35])[CH2:20][CH3:21])=[N:11]1.[NH:40]1[CH:44]=[CH:43][N:42]=[CH:41]1.CO>C(OCC)(=O)C>[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]([N:40]2[CH:44]=[CH:43][N:42]=[CH:41]2)[C:12]([NH:17][C:18](=[O:39])[CH:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH2:32][CH3:33])([CH3:31])[CH3:30])=[CH:25][C:24]=2[C:34]([CH2:37][CH3:38])([CH3:36])[CH3:35])[CH2:20][CH3:21])=[N:11]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 887MethanolHCID 20301304HCID 20301304, compound

Product 1

HCID 20555349HCID 20555349, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

66 g (0.1 mol) of 1-(2,4,6-trichlorophenyl)-3-[α-(2,4-di-tert-amylphenoxy)butyramido]-4-bromo-5-oxo-2-pyrazoline and 27.2 g (0.4 mol) of imidazole were well mixed with each other in a mortar, then stirred for 2 hours under heating to 100° C. To the reaction mixture was added 200 ml of methanol to prepare a solution. Then 1 liter of ethyl acetate was added thereto, followed by washing several times with water. The ethyl acetate layer was dried with anhydrous sodium sulfate, and concentrated. Upon crystallization of the residue from acetonitrile-ethyl acetate (volume ratio:20.1), 48 g of pure Coupler (1) was obtained. The melting point of the coupler was 185°-187° C.

Workup

  1. customto prepare a solution
  2. washby washing several times with water
  3. dry with materialThe ethyl acetate layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customUpon crystallization of the residue from acetonitrile-ethyl acetate (volume ratio:20.1), 48 g of pure Coupler (1)
  6. customwas obtained
  7. customwas 185°-187° C.

Sources & evidence

ORD record
ord-d81a5b7216c6484c9a7e9025b4e0d97a
Source dataset
uspto-grants-1980_12
Patent number
US04241168

Reaction notes

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