4,4-Diaminodiphenylmethane → HCID 2803143, compound

HRID 2419198Notes

Reaction equation

HRID 2419198 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:16](=O)/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH:16](=[N:13][C:12]1[CH:14]=[CH:15][C:9]([CH2:1][C:2]2[CH:3]=[CH:4][C:5]([N:6]=[CH:10][CH:9]=[CH:1][C:2]3[CH:8]=[CH:7][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH:8]=2)=[CH:10][CH:11]=1)[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 75774,4-DiaminodiphenylmethaneHCID 637511Cinnamaldehyde

Product 1

HCID 2803143HCID 2803143, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 198.2 g (1 mole) of 4,4'-methylene dianiline in 2000 ml of ethanol was added a solution of 277.6 g (2.1 moles) of trans-cinnamaldehyde in 500 ml of ethanol over a 2 minute period. Immediately an exothermic reaction ensued and within 2 minutes the reaction mixture set up to a yellow solid. An additional 1000 ml of ethanol was added, the reaction mixture was heated at reflux for 1 hour with stirring, and then cooled to room temperature. The product was filtered and dried in vacuum at room temperature, yielding 402.5 l g (94% of theory) of N,N'-biscinnamal-4,4'-methylene dianiline, m.p. 162.5°-163.5° C.

Workup

  1. customImmediately an exothermic reaction
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. filtrationThe product was filtered
  5. customdried in vacuum at room temperature

Sources & evidence

ORD record
ord-311415861dfe4fc3b02286f55b3e2795
Source dataset
uspto-grants-1978_08
Patent number
US04105646

Reaction notes

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