4-Isopropylaniline → 2-Bromo-2-methyl-N-[4-(propan-2-yl)phenyl]pentanamide

HRID 462840Notes

Reaction equation

HRID 462840 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:18][C:19]([CH3:26])([CH2:23][CH2:24][CH3:25])[C:20](Cl)=[O:21]>C1C=CC=CC=1>[Br:18][C:19]([CH3:26])([CH2:23][CH2:24][CH3:25])[C:20]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)=[O:21]

Participants

5

Reactant 3

HCID 74644-IsopropylanilineHCID 8471TriethylamineHCID 13472016HCID 13472016, compound

Product 1

HCID 134720172-Bromo-2-methyl-N-[4-(propan-2-yl)phenyl]pentanamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

410 mg (3.04 mmoles) of 4-isopropylaniline was dissolved in 10 ml of benzene, and 500 mg of triethylamine was added. With stirring under ice cooling, 800 mg (4.10 mmoles) of 2-bromo-2-methylvaleryl chloride was added dropwise. After the addition, the mixture was further stirred at room temperature for 1 hour. The crystals that precipitated were separated by filtration. The filtrate was concentrated, and the residue was recrystallized from benzene to give 620 mg of 2-bromo-2-methyl-4'-isopropylvaleranilide. m.p. 87.2°-88.2° C. IR νmaxcm-1 3300 and 1650. Yield 65.4%.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was further stirred at room temperature for 1 hour
  3. customThe crystals that precipitated
  4. customwere separated by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-4083ea7875c048288555b100116def86
Source dataset
uspto-grants-1985_05
Patent number
US04517381

Reaction notes

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