Propanoyl bromide, 2-bromo- → 2-Bromo-N-(4-butoxy-2,6-dimethylphenyl)propanamide

HRID 2397836Notes

Reaction equation

HRID 2397836 reaction equation
[CH2:1]([O:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:9]([NH2:10])=[C:8]([CH3:14])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[Br:15][CH:16]([CH3:20])[C:17](Br)=[O:18].O.O.O.C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[Br:15][CH:16]([CH3:20])[C:17]([NH:10][C:9]1[C:11]([CH3:13])=[CH:12][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][C:8]=1[CH3:14])=[O:18]

Participants

6

Reactant 3

HCID 79047Propanoyl bromide, 2-bromo-HCID 12546818HCID 12546818, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 125468282-Bromo-N-(4-butoxy-2,6-dimethylphenyl)propanamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a chilled (ca 10° ) solution of 50.7 g (0.263 mole) of 4-butoxy-2,6-dimethylaniline [Buchi et al., Helv. Chim. Acta, 34, 278 (1951)] in 224 ml glacial acetic acid was added rapidly 62.4 g (.289 mole) of 2-bromo-propionyl bromide and immediately thereafter a chilled (ca 5° ) solution of 87.2 g sodium acetate trihydrate in 362 ml water. This mixture was shaken for 1/2 hour, filtered, washed with water until the washes were neutral, and dried in vacuo over silica gel and KOH; yield 68.9 g (71.6%); m.p. 132.5° - 133.5°. The product was recrystallized from 95% ethanol; m.p. 135.5° - 136°.

Workup

  1. filtrationfiltered
  2. washwashed with water until the washes
  3. dry with materialdried in vacuo over silica gel and KOH
  4. customThe product was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-27423e14694d450e98e5699210fc7f52
Source dataset
uspto-grants-1977_05
Patent number
US04022899

Reaction notes

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