Hydrochloric Acid → 1-(2,4,6-Trichlorophenyl)-2-acetyl-3-(2-chloro-5-myristoylaminoanilino)-3-pyrazolin-5-one

HRID 460736Notes

Reaction equation

HRID 460736 reaction equation
N1C(C)=CC=CC=1C.[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[C:11]=1[N:18]1[C:22](=[O:23])[CH2:21][C:20]([NH:24][C:25]2[CH:30]=[C:29]([NH:31][C:32](=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:28]=[CH:27][C:26]=2[Cl:47])=[N:19]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:52](Cl)(=[O:54])[CH3:53].Cl>ClCCl>[Cl:17][C:12]1[CH:13]=[C:14]([Cl:16])[CH:15]=[C:10]([Cl:9])[C:11]=1[N:18]1[C:22](=[O:23])[CH:21]=[C:20]([NH:24][C:25]2[CH:30]=[C:29]([NH:31][C:32](=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:28]=[CH:27][C:26]=2[Cl:47])[N:19]1[C:52](=[O:54])[CH3:53]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 79372,6-Lutidine2×HCID 6451240Aluminum(III) ChlorideHCID 178443172N-[4-chloro-3-[[5-oxo-1-(2,4,6-trichlorophenyl)-4H-pyrazol-3-yl]amino]phenyl]tetradecanamide

Product 1

HCID 213940501-(2,4,6-Trichlorophenyl)-2-acetyl-3-(2-chloro-5-myristoylaminoanilino)-3-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

1.07 g (0.01 mole) of lutidine is added to a solution of 30.7 g (0.05 mole) of 1-(2,4,6-trichlorophenyl)-3-(2-chloro-5-myristoylaminoanilino)-2-pyrazolin-5-one and 8 g (0.06 mole) of anhydrous aluminium chloride in 100 ml of dichloromethane. The solution is cooled to 10° C and 5.90 g (0.075 mole) of acetylchloride are added. 8 g (0.075 mole) of lutidine divided into 4 portions of 2 g each (one portion every 15 min) are added in a total period of time of 1 h, the temperature being kept below 10° C. The reaction mixture is stirred for 2 h more and then poured out into 1 l of 1N aqueous hydrochloric acid. The dichloromethane layer is washed until free from acid, dried, and concentrated by evaporation. The product is agitated with methanol.

Workup

  1. customevery 15 min
  2. additionare added in a total period of time of 1 h
  3. custombeing kept below 10° C
  4. washThe dichloromethane layer is washed until free from acid
  5. customdried
  6. concentrationconcentrated by evaporation
  7. stirringThe product is agitated with methanol

Sources & evidence

ORD record
ord-1e047ed0942046248435f195249898c6
Source dataset
uspto-grants-1977_12
Patent number
US04061498

Reaction notes

Loading…