Nitric Acid → N-(4-(1,1-Dimethylethyl)-2-nitrophenyl)acetamide

HRID 1424239Notes

Reaction equation

HRID 1424239 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([N+:22]([O-:24])=[O:23])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 140672p-t-Butylacetanilide

Product 1

HCID 97069N-(4-(1,1-Dimethylethyl)-2-nitrophenyl)acetamideYield 95.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A reactor was charged with acetic acid (8.7 L), followed by N-(4-tert-butylphenyl) acetamide (Preparation 110, 6.0 kg, 31.4 mol), The mixture was stirred for ten minutes, followed by the addition of acetic anhydride (6.47 kg, 63.4 mol) slowly at room temperature. The reaction was stirred for fifteen minutes. A solution of fuming nitric acid (3.56 kg, 56.5 mol) in acetic acid (2.1 L) was added slowly at 20-25° C., and stirred at that temperature for another 2 hours. The reaction mixture was added to ice water (42 L) at 10-15° C. and the mixture stirred for one hour. The resulting solids were collected by filtration, washed with water (17 L) and dried at 65-70° C. to provide 7.1 kg of the title compound.

Workup

  1. stirringThe reaction was stirred for fifteen minutes
  2. stirringstirred at that temperature for another 2 hours
  3. stirringthe mixture stirred for one hour
  4. filtrationThe resulting solids were collected by filtration
  5. washwashed with water (17 L)
  6. customdried at 65-70° C.

Sources & evidence

ORD record
ord-e785db7f392543eaaceeae56e2d7343e
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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