Acetic Anhydride → HCID 67485214, compound

HRID 2057073Notes

Reaction equation

HRID 2057073 reaction equation
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:14]([O:17]C(=O)C)(=O)[CH3:15].[N+:21]([O-])([O-:23])=[O:22].[K+]>S(=O)(=O)(O)O>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:11][C:14](=[O:17])[CH3:15])=[C:12]([N+:21]([O-:23])=[O:22])[CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24434Potassium NitrateHCID 807644-Cyclohexylbenzenamine

Product 1

HCID 67485214HCID 67485214, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-cyclohexylaniline (10.0 g, 57.1 mmol) and acetic anhydride (50 ml) was stirred at 50° C. for 1 hour. The resultant mixture was cooled in an ice-bath and a solution of potassium nitrate (10.0 g, 99.0 mmol) in conc. sulphuric acid (25 ml) was added drop-wise keeping the temperature at 15-18° C. After the addition, the mixture was poured into ice-water (400 g). The precipitate was filtered off, washed with water and dried. This crude product (12 g) contained a 1:1 mixture of mono- and dinitrated product. The desired product was isolated by column chromatography on silica gel, using a mixture of petroleum ether and ethyl acetate (9:1, v/v) as the eluent (6.5 g).

Workup

  1. customat 15-18° C
  2. additionAfter the addition
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. additiona 1:1 mixture of mono- and dinitrated product

Sources & evidence

ORD record
ord-6bba3d8f3f134279831379a5e9c17142
Source dataset
uspto-grants-2008_02
Patent number
US07335777B2

Reaction notes

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