2-Aminothiophenol → 6344-17-8

HRID 1283292Notes

Reaction equation

HRID 1283292 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Br:9][C:10]1[CH:17]=[C:14]([CH:15]=O)[C:13]([OH:18])=[CH:12][CH:11]=1>N1C=CC=CC=1>[OH:18][C:13]1[CH:12]=[CH:11][C:10]([Br:9])=[CH:17][C:14]=1[C:15]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 728635-Bromosalicylaldehyde

Product 1

HCID 2420576344-17-8

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminothiophenol (12.5 g, 0.1 mole) was dissolved in 30 ml. of pyridine and 20.1 g (0.1 mole) of 5-bromosalicylaldehyde was added dropwise during 15 minutes. The solution was warmed on a steam bath for 2 hours and then a stream of air was bubbled through the mixture while heating for another hour. The mixture was poured into 300 ml. of 2 N HCl which was then stirred until crystals formed. The product was removed by filtration, washed with water and recrystallized from ethanol, mp. 164°-165°. Yield, 8.0 g. (26%).

Workup

  1. temperatureThe solution was warmed on a steam bath for 2 hours
  2. customa stream of air was bubbled through the mixture
  3. temperaturewhile heating for another hour
  4. additionThe mixture was poured into 300 ml
  5. customformed
  6. customThe product was removed by filtration
  7. washwashed with water
  8. customrecrystallized from ethanol, mp. 164°-165°
  9. customYield

Sources & evidence

ORD record
ord-744b8c70f0294a1282161eb9dbfeb8cf
Source dataset
uspto-grants-1976_08
Patent number
US03974287

Reaction notes

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