M-Phenylenediamine → HCID 88829827, compound

HRID 441279Notes

Reaction equation

HRID 441279 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]1([NH2:14])[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1>O1CCCC1>[C:4]([NH:14][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH3:3].[C:2]([CH2:3][C:4]([NH:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[NH:14][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])=[O:5])(=[O:6])[CH3:1]

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 12661Diketene

Product 1

HCID 88829827HCID 88829827, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

168 g of diketene were slowly added to a solution of 108 g of m-phenylenediamine in a liter of tetrahydrofuran and the mixture was stirred for 5 hours at 20° C. and then was allowed to stand for 15 hours. The mixture was concentrated to dryness under reduced pressure and the residue was added to methanol. The mixture was vacuum filtered and the recovered precipitate was dried to obtain 180 g of m-(acetylacetamido)-acetyl-acetanilide acetanilide melting at 117° C. Chromatography over silica gel and elution with a 6- 4 methylene chloride-acetone mixture gave a product melting at 118° C.

Workup

  1. waitto stand for 15 hours
  2. concentrationThe mixture was concentrated to dryness under reduced pressure
  3. additionthe residue was added to methanol
  4. filtrationfiltered
  5. customthe recovered precipitate was dried

Sources & evidence

ORD record
ord-07d283dde4c24fffaff0134fe92a8083
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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