Boric Acid → Acetamide, N,N'-(azodi-4,1-phenylene)bis-

HRID 838841Notes

Reaction equation

HRID 838841 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)=[O:3].B(O[O-])=O.[Na+].B(O)(O)O>C(O)(=O)C>[NH:4]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:11][C:8]2[CH:7]=[CH:6][C:5]([NH:4][C:2]([CH3:1])=[O:3])=[CH:10][CH:9]=2)=[CH:7][CH:6]=1)[C:2]([CH3:1])=[O:3]

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 312304-AminoacetanilideHCID 517072Sodium Perborate

Product 1

HCID 27289Acetamide, N,N'-(azodi-4,1-phenylene)bis-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

69 parts of 82% pure 4-aminoacetanilide, 80 parts of sodium perborate and 20 parts of boric acid in 1,000 parts by volume of glacial acetic acid are stirred at room temperature. After 5 minutes, a violet solution is produced, which is heated to 60°. At this temperature, an exothermic reaction takes place, and the temperature rises, without heating, to 70°. A beige precipitate separates out. The suspension thus obtained is stirred for a further 6 hours at 60° and is then cooled to 20° and filtered. The filter residue is washed with water until neutral and is dried in vacuo at 60°. The product is a beige powder which melts between 286° and 290°, with decomposition. The yield is 39.4 parts (70% of theory).

Workup

  1. customa violet solution is produced
  2. temperaturewhich is heated to 60°
  3. customAt this temperature, an exothermic reaction
  4. temperaturewithout heating, to 70°
  5. customThe suspension thus obtained
  6. temperatureis then cooled to 20°
  7. filtrationfiltered
  8. washThe filter residue is washed with water until neutral and
  9. customis dried in vacuo at 60°

Sources & evidence

ORD record
ord-e0da6da5f7e145d0b80676545c23ceb9
Source dataset
uspto-grants-1978_06
Patent number
US04093613

Reaction notes

Loading…