Butyryl chloride → HCID 20556958, compound

HRID 1660538Notes

Reaction equation

HRID 1660538 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]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C:12]([NH:21][C:22]2[CH:27]=[C:26]([NH:28][C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:25]=[CH:24][C:23]=2[Cl:44])=[N:11]1.[C:45](Cl)(=[O:49])[CH2:46][CH2:47][CH3:48].C(OCC)(=O)C>C(#N)C>[C:45]([O:15][C:14]1[N:10]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=2[Cl:9])[N:11]=[C:12]([NH:21][C:22]2[CH:27]=[C:26]([NH:28][C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:25]=[CH:24][C:23]=2[Cl:44])[C:13]=1[N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)(=[O:49])[CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 178443174HCID 178443174, compound

Product 1

HCID 20556958HCID 20556958, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20 g of 1-(2,4,6-trichlorophenyl)-3-(2-chloro-5-tetradecanamidoanilino)-4-(1,2,4-triazol-1-yl)-5-oxo-2-pyrazoline (prepared by the method described in U.S. Pat. No. 4,076,533) was suspended in 100 ml of acetonitrile and 3.7 g of butanoyl chloride was added to the mixture, followed by refluxing for 3 hours. After cooling to room temperature, 500 ml of ethyl acetate was added to the reaction mixture and 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 benzene, 16 g of Coupler (1) was obtained. The melting point of the coupler was 89° to 95° C.

Workup

  1. temperatureby refluxing for 3 hours
  2. washwashed 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
  6. additionfrom a solvent mixture of acetonitrile and benzene, 16 g of Coupler (1)
  7. customwas obtained
  8. customwas 89° to 95° C.

Sources & evidence

ORD record
ord-f0c03a8986834ec1a7036d33be19d7b2
Source dataset
uspto-grants-1981_12
Patent number
US04308343

Reaction notes

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