Acetic Acid → 2-Bromo-N-(4-butoxy-2,6-dimethylphenyl)propanamide

HRID 1856291Notes

Reaction equation

HRID 1856291 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].C(O)(=O)C.[Br:19][CH:20]([CH3:24])[C:21](Br)=[O:22].O.O.O.C([O-])(=O)C.[Na+]>O>[Br:19][CH:20]([CH3:24])[C:21]([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:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 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 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

In a two liter bottle were mixed 4-butoxy-2,6-dimethylaniline (50.7 g, 0.263 mole) and glacial acetic acid (224 ml) and the mixture was cooled to about 10° C. To this was added and mixed rapidly 2-bromopropionyl bromide (62.4 g, 0.289 mole) immediately followed by a precooled (5° C.) solution of sodium acetate trihydrate (87.2 g) in water (362 ml). The whole was vigorously shaken to ensure intimate mixture of the components. After 30 min. of mechanical shaking, the precipitate was filtered off and washed carefully with distilled water. It was thereafter dried. The yield was 68.9 g (72%). Recrystallized from 95% ethanol, it melted at 135.5°-136°. Calcd. for C15H22BrNO2 : C 54.9, H 6.75, Br 24.3. Found: C 55.1, H 6.22, Br 24.7.

Workup

  1. additionTo this was added
  2. additionmixture of the components
  3. filtrationthe precipitate was filtered off
  4. washwashed carefully with distilled water
  5. customIt was thereafter dried
  6. customRecrystallized from 95% ethanol, it melted at 135.5°-136°

Sources & evidence

ORD record
ord-729e618e3eaf4a3fbbfa46bc3706a7f1
Source dataset
uspto-grants-1980_08
Patent number
US04218477

Reaction notes

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