Sulfuric Acid → HCID 68378991, compound

HRID 2172709Notes

Reaction equation

HRID 2172709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:12])(O)[CH3:10])=[CH:4][CH:3]=1.[Cl:13][CH2:14][C:15]#[N:16].S(=O)(=O)(O)[OH:18].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Cl:13][CH2:14][C:15]([NH:16][C:9]([CH3:12])([CH3:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 796094-Chloro-alpha,alpha-dimethylphenethylic alcohol

Product 1

HCID 68378991HCID 68378991, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the crude alcohol (184 mg, 0.996 mmol) and chloroacetonitrile (150 mg, 1.99 mmol) in acetic acid (3.0 mL) was cooled to 0° C. Concentrated sulfuric acid (1.0 mL) was added to the solution dropwise while keeping the reaction temperature below 10° C. After stirring at room temperature for 1 hour, the resulting solution was poured onto ice and basified by the addition of solid potassium carbonate to pH>8. The mixture was extracted with ethyl acetate and the combined organic fractions were washed with water, dried over sodium sulfate and concentrated under vacuum to give 150 mg of 2-chloro-N -(1-(4-chlorophenyl)-2-methylpropan-2-yl)acetamide as yellow solid. The crude material was used directly in the next step.

Workup

  1. customthe reaction temperature below 10° C
  2. additionthe resulting solution was poured onto ice
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic fractions were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2537944778f24c559362790c368dd3e8
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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