Sulfuric Acid → HCID 59410108, compound

HRID 1805115Notes

Reaction equation

HRID 1805115 reaction equation
N[C:2]1[CH:3]=[C:4]([NH:14]C(=O)C)[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[OH:18]S(O)(=O)=O.N([O-])=O.[Na+].NC(N)=O>O>[NH2:14][C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:2]([OH:18])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 23668193Sodium NitriteHCID 59410068HCID 59410068, compound

Product 1

HCID 59410108HCID 59410108, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

N-(3-amino-4-cyclohexyl-phenyl)acetamide (696 mg, 3.0 mmol) was added dropwise to a mixture of conc.H2SO4 (3 mL, 56.28 mmol) and H2O (17 mL). This reaction mixture was cooled to 0° C. and a solution of NaNO2 (229 mg, 3.32 mmol) in H2O (2 mL) was added. The reaction mixture was stirred for 5 minutes at 0° C. and then 1 g of urea was added, followed by the addition of 10 mL of 1:2H2SO4:H2O. The reaction mixture was then refluxed for 1 hour, cooled to room temperature and extracted with EtOAc. The aqueous layer was basified with solid NaOH and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to obtain 5-amino-2-cyclohexylphenol (426 mg, 74%), which was used without further purification.

Workup

  1. additionfollowed by the addition of 10 mL of 1:2H2SO4
  2. temperatureThe reaction mixture was then refluxed for 1 hour
  3. temperaturecooled to room temperature
  4. extractionextracted with EtOAc
  5. extractionextracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9066d10a6c3548f191842328471430ba
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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