Acetamide, N-(2-iodo-4-nitrophenyl)- → HCID 12335772, compound

HRID 259493Notes

Reaction equation

HRID 259493 reaction equation
I[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]>CN(C=O)C>[C:5]([NH:4][C:3]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:2]=1[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6])(=[O:7])[CH3:6]

Participants

3

Reactant 1

HCID 4400707Acetamide, N-(2-iodo-4-nitrophenyl)-

Product 1

HCID 12335772HCID 12335772, compoundYield 116.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2'-iodo-4'-nitroacetanilide (II) (50.02 g, 0.164 mole), copper-bronze (87.9 g) and N,N'-dimethylformamide (350 ml) was stirred and heated at 150° C. under nitrogen for 1 hour and filtered. The filter cake was washed with tetrahydrofuran, and the combined filtrate and washings were concentrated under vacuum to 100 ml and poured, with stirring, into 1200 ml of concentrated ammonium hydroxide. The resultant precipitate was filtered, washed with water, and dried at 100° C. and 1 mm Hg to yield 34.1 g (58 %) of 2,2'-bis-(acetamido)-5,5'-dinitrobiphenyl. An analytical sample, m.p. 263°- 265° C., was obtained by recrystallization from ethanol.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with tetrahydrofuran
  3. concentrationthe combined filtrate and washings were concentrated under vacuum to 100 ml
  4. additionpoured
  5. stirringwith stirring, into 1200 ml of concentrated ammonium hydroxide
  6. filtrationThe resultant precipitate was filtered
  7. washwashed with water
  8. customdried at 100° C.

Sources & evidence

ORD record
ord-ed28c9f05fce4175a7317fba8800442b
Source dataset
uspto-grants-1977_07
Patent number
US04038320

Reaction notes

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