Acetic Acid → N-(2,5-Difluoro-4-nitrophenyl)acetamide

HRID 1078004Notes

Reaction equation

HRID 1078004 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:7]=1[NH:8][C:9](=[O:11])[CH3:10].C(O)(=O)C>S(=O)(=O)(O)O>[F:5][C:6]1[CH:15]=[C:14]([N+:1]([O-:4])=[O:2])[C:13]([F:16])=[CH:12][C:7]=1[NH:8][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 242830n-(2,5-difluorophenyl)acetamide

Product 1

HCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of nitric acid (21.85 mL) and sulfuric acid (28.5 mL) is added dropwise to a mixture of 2',5'-difluoroacetanilide (44.2 g, 0.281 mol) and acetic acid (19 mL) in sulfuric acid (190 mL) while maintaining the reaction mixture temperature below 10° C. After the addition is complete, the reaction mixture is stirred at 0° C. for one hour and poured onto cracked ice (2 L). The aqueous mixture is filtered to obtain a solid. The solid is air dried and recrystallized from ethanol to give the title product as a yellow, crystalline solid, mp 188°-189° C.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 10° C
  2. additionAfter the addition
  3. additionpoured
  4. filtrationThe aqueous mixture is filtered
  5. customto obtain a solid
  6. customdried
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2834c1dd986b45a4af183ad3840871cf
Source dataset
uspto-grants-1996_08
Patent number
US05545742

Reaction notes

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