Ammonia → 4-Styrylphenylamine

HRID 1414440Notes

Reaction equation

HRID 1414440 reaction equation
[CH:1]([C:9]1[CH:14]=[CH:13][C:12](S([O-])(=O)=O)=[CH:11][CH:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na+].[NH2-:20].[Na+].N>>[NH2:20][C:12]1[CH:13]=[CH:14][C:9]([CH:1]=[CH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 86734358HCID 86734358, compound

Product 1

HCID 132654-StyrylphenylamineYield 101.6%

Procedure

In a 200-ml autoclave were placed 18.6 grams (0.06 mole) of anhydrous sodium p-styrylbenzene sulfonate, 5.2 grams (0.13 mole) of sodium amide and 50 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 120° C for 6 hours. The reaction pressure in the autoclave was 90 atm. during the reaction. After the ammonia was removed, 10 ml of water was added to the reaction mixture for hydrolysis. The product was extracted with ether and the ether was distilled off to produce crude 4-aminostilbene. The recrystallization thereof from ethanol gave 11.9 grams of 4-aminostilbene having a melting point of 151° to 152° C. Yield was 88.5%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition10 ml of water was added to the reaction mixture for hydrolysis
  5. extractionThe product was extracted with ether
  6. distillationthe ether was distilled off
  7. customto produce crude 4-aminostilbene
  8. customThe recrystallization

Sources & evidence

ORD record
ord-f76d50521b3e406ab3806b3a917fbcc8
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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