Sulfuric Acid → HCID 22124971, compound

HRID 1858320Notes

Reaction equation

HRID 1858320 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:12])(O)[CH3:10])=[CH:4][CH:3]=1.[C:13](#[N:15])[CH3:14].S(=O)(=O)(O)[OH:17].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:15][C:13](=[O:17])[CH3:14])([CH3:12])[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 3167851-(4-Bromophenyl)-2-methylpropan-2-ol

Product 1

HCID 22124971HCID 22124971, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.5 g (15.4 mmol) of 1-(4-bromophenyl)-2-methyl-propan-2-ol in 20 ml of glacial acetic acid was treated with 630 mg (15.4 mmol) of acetonitrile and cooled in ice. 10 ml of concentrated sulfuric acid was added slowly and the mixture stirred for 72 hours. The mixture was poured into 300 ml of ice/water and neutralised with potassium carbonate. The product was extracted with diethyl ether (2×250 ml). The combined organic phases were dried over magnesium sulfate, filtered and evaporated. The product was purified by recrystallisation from diethyl ether/hexane to give 3.3 g (80%) of N-[2-(4-bromophenyl)-1,1-dimethyl-ethyl]acetamide as a white solid. [Mass spectrum (ESI) MH+ =270].

Workup

  1. temperaturecooled in ice
  2. extractionThe product was extracted with diethyl ether (2×250 ml)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was purified by recrystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-6989556466be43bc948ee7dfb9a9a24e
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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