Water → HCID 178443175, compound

HRID 1248962Notes

Reaction equation

HRID 1248962 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:39])[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])=[CH:20][C:3]=1[NH:4][C:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:12]=2[Cl:19])[N:6]=1.[C:40]([C:43]1[CH:44]=[C:45]([N:49]2[C:53]([SH:54])=[N:52][N:51]=[N:50]2)[CH:46]=[CH:47][CH:48]=1)([OH:42])=[O:41].BrN1C(=O)CCC1=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:39])[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])=[CH:20][C:3]=1[NH:4][C:5]1[CH:9]([S:54][C:53]2[N:49]([C:45]3[CH:46]=[CH:47][CH:48]=[C:43]([C:40]([OH:42])=[O:41])[CH:44]=3)[N:50]=[N:51][N:52]=2)[C:8](=[O:10])[N:7]([C:11]2[C:12]([Cl:19])=[CH:13][C:14]([Cl:18])=[CH:15][C:16]=2[Cl:17])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 178418535HCID 178418535, compoundHCID 178443172N-[4-chloro-3-[[5-oxo-1-(2,4,6-trichlorophenyl)-4H-pyrazol-3-yl]amino]phenyl]tetradecanamide

Product 1

HCID 178443175HCID 178443175, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15 g of 3-(2-chloro-5-tetradecanamidoanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one and 5.4 g of 1-(3-carboxyphenyl)-5-mercaptotetrazole were dissolved in 100 ml of DMF and to the solution was added dropwise at room temperature 20 ml of a DMF solution containing 4.9 g of N-bromosuccinimide. After stirring for 30 minutes, 500 ml of water was added to the mixture which was extracted with ethyl acetate. The ethyl acetate was distilled off under reduced pressure and the residue was crystallized from a solvent mixture of ethyl acetate and acetonitrile to obtain 14 g of 3-(2-chloro-5-tetradecanamidoanilino)-1-(2,4,6-trichlorophenyl)-4-[1-(3-carboxyphenyl)-5-tetrazolylthio]-2-pyrazolin-5-one. Yield: 68%. Melting Point: 155° to 165° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. distillationThe ethyl acetate was distilled off under reduced pressure
  3. customthe residue was crystallized from a solvent mixture of ethyl acetate and acetonitrile

Sources & evidence

ORD record
ord-45d5339bc1d446b399326adad2cd80f2
Source dataset
uspto-grants-1986_12
Patent number
US04628024

Reaction notes

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