Acetic Acid → Acetamide, N,N'-m-phenylenebis- (6CI,7CI,8CI)

HRID 1976518Notes

Reaction equation

HRID 1976518 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[C:5]1([NH2:12])[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>O>[C:13]([NH:11][C:7]1[CH:6]=[C:5]([NH:12][C:1](=[O:4])[CH3:2])[CH:10]=[CH:9][CH:8]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 7935M-Phenylenediamine

Product 1

HCID 82506Acetamide, N,N'-m-phenylenebis- (6CI,7CI,8CI)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 1-liter reaction flask cooled with an ice bath was introduced 35 ml of acetic acid. Thereto was gradually added 15 g (138.7 mmol) of m-phenylenediamine. Thereto was dropwise added 2 ml (307.4 mmol) of acetic anhydride at room temperature to 30° C. After completion of the addition, the mixture was stirred at 60° C. for 1 hour and then poured into 150 ml of water. The resultant precipitate was taken out by filtration, sufficiently washed with water, and then dried to obtain 18.4 g of diacetyl-m-phenylenediamine as the target compound.

Workup

  1. customInto a 1-liter reaction flask
  2. temperaturecooled with an ice bath
  3. customat room temperature to 30° C
  4. additionAfter completion of the addition
  5. filtrationThe resultant precipitate was taken out by filtration
  6. washsufficiently washed with water
  7. customdried

Sources & evidence

ORD record
ord-de2bd2aee715422b84105e32366945a7
Source dataset
uspto-grants-2001_05
Patent number
US06228547B1

Reaction notes

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