3,3'-Diaminobenzidine → HCID 18436489, compound

HRID 456362

Reaction equation

HRID 456362 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]>C1(=O)CCCCC1>[C:2]1(=[NH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1.[C:2]1(=[NH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1.[C:2]1(=[NH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1.[C:2]1(=[NH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1.[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

3

Reactant 1

HCID 70713,3'-Diaminobenzidine

Product 1

HCID 18436489HCID 18436489, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Conditions

Temperature
60 °C

Procedure

In a 200-ml flask equipped with a stirrer, a condenser and a thermometer were placed 21.4 g (100 mmol) of 3,3′-diaminobenzidine and 100 ml of cyclohexanone, followed by heating with stirring at 60° C. in a nitrogen atmosphere for 2 hours. After cooling to room temperature, cyclohexanone was removed under reduced pressure. The residue was purified by silica gel chromatography, to yield 48.1 g (90 mmol) of the target 3,3′-diaminobenzidine tetracyclohexanimine [N,N′,N″,N′″-tetracyclohexylidene-3,4,3′,4′-biphenyltetramine] in a yield of 90%.

Workup

  1. customIn a 200-ml flask equipped with a stirrer, a condenser
  2. temperatureby heating
  3. temperatureAfter cooling to room temperature
  4. customcyclohexanone was removed under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a4e875c34afd4f75a4db895afccd1b3b
Source dataset
uspto-grants-2007_03
Patent number
US07186454B2

Linked notes

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