Ethanol → 4-(1-Phenylethenyl)benzene-1,2-diamine

HRID 1903176Notes

Reaction equation

HRID 1903176 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:9])=[CH:4][C:3]=1[N+:16]([O-])=O.C(O)C.[Na+].[SH-]>O>[NH2:16][C:3]1[CH:4]=[C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH2:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 28015Sodium hydrosulfideHCID 132776142-Nitro-4-(1-phenylethenyl)aniline

Product 1

HCID 132776154-(1-Phenylethenyl)benzene-1,2-diamineYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(4-Amino-3-nitrophenyl)-1-phenylethylene (7.7 g., 0.032 mole) was dissolved in refluxing ethanol (450 ml.). To this was added, dropwise, a solution of sodium sulfhydrate (38.5 g., 0.45 mole) in water (110 ml.). The resulting solution was refluxed overnight. The solution was diluted with water (1 l.), cooled, and filtered yielding 1-(3,4-diaminophenyl)-1-phenylethylene: 5.6 g., 83% yield, m.p. 109°-110°.

Workup

  1. additionTo this was added
  2. temperatureThe resulting solution was refluxed overnight
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2423a7a5e80a4b98ace2bdabf9b1d4c7
Source dataset
uspto-grants-1984_03
Patent number
US04435418

Reaction notes

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