Toluene → N-(3-Chloro-4-propan-2-ylphenyl)-2-methylpentanamide

HRID 579860Notes

Reaction equation

HRID 579860 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH:16]([CH3:18])[CH3:17])[NH2:12].[CH3:19][CH:20]([CH2:24][CH2:25][CH3:26])[C:21](Cl)=[O:22]>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([NH:12][C:21](=[O:22])[CH:20]([CH3:19])[CH2:24][CH2:25][CH3:26])[CH:13]=[CH:14][C:15]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 1073852-Methylvaleryl chlorideHCID 139133463-Chloro-4-isopropylaniline

Product 1

HCID 184733N-(3-Chloro-4-propan-2-ylphenyl)-2-methylpentanamideYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 36 ml of toluene were added 1.0 g (5.9/1000 mole) of 3-chloro-4-isopropylaniline and 0.7 g of pyridine, and 0.9 g (5.9/1000 mole) of 2-methylvaleryl chloride was added. The mixture was stirred at room temperature for 20 minutes. The crystals that precipitated were separated by filtration. Water (70 ml) was added to the filtrate, and the mixture was extracted with toluene. The toluene solution was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. The resulting dried solution was concentrated by an evaporator. Recrystallization of the resulting crude crystals from methanol gave 1.2 g of N-(3-chloro-4-isopropylphenyl)-2-methylvaleramide in a yield of 76.0 % based on 3-chloro-4-isopropylaniline.

Workup

  1. additionwas added
  2. customThe crystals that precipitated
  3. customwere separated by filtration
  4. additionWater (70 ml) was added to the filtrate
  5. extractionthe mixture was extracted with toluene
  6. washThe toluene solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe resulting dried solution was concentrated by an evaporator
  9. customRecrystallization of the resulting crude crystals from methanol

Sources & evidence

ORD record
ord-31833a5d11bb47c086fb3a96d1dedd43
Source dataset
uspto-grants-1988_06
Patent number
US04749812

Reaction notes

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