Sulfuric Acid → HCID 68379017, compound

HRID 2172717Notes

Reaction equation

HRID 2172717 reaction equation
[CH3:1][C:2](O)([CH3:14])[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.S(=O)(=O)(O)[OH:17].[C:21](#[N:23])[CH3:22]>O>[CH3:1][C:2]([NH:23][C:21](=[O:17])[CH3:22])([CH3:14])[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 10798101HCID 10798101, compound

Product 1

HCID 68379017HCID 68379017, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude alcohol (2.0 g, 10 mmol) was dissolved in acetonitrile (10 mL) and concentrated sulfuric acid (4.9 g, 50 mmol) was added dropwise at 0° C. After stirring at room temperature for 2 hours, the reaction mixture was diluted with water and extracted with dichloromethane. The combined organic fractions were dried over sodium sulfate and evaporated. The residue was purified by silical gel column chromatography (petroleum ether/ethyl acetate) to give N—(2-methyl-1-(naphthalene-1-yl)propan-2-yl)acetamide (0.90 g, 37% yield) as a yellow solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by silical gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-559c81dbab654201b413b12e52ff93ad
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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