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

HRID 1903746Notes

Reaction equation

HRID 1903746 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 reaction mixture 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-4e53d29e0cb3486e8fbb916fba1568ee
Source dataset
uspto-grants-1984_03
Patent number
US04438135

Reaction notes

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