Ammonium Hydroxide → HCID 12736997, compound

HRID 507692Notes

Reaction equation

HRID 507692 reaction equation
[C:1]1([CH:7](O)[CH2:8][NH:9][CH2:10][C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+]>>[C:1]1([CH:7]2[CH2:8][NH:9][CH2:10][C:11]3[CH:15]=[CH:14][S:13][C:12]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 4723863HCID 4723863, compound

Product 1

HCID 12736997HCID 12736997, compound

Conditions

Temperature
80 °C

Procedure

1-Phenyl-2-(thiophen-3-ylmethylamino)ethanol (4.5 g, 19.2 mmol) was added to a flask containing polyphosphoric acid (20 g) and the mixture was heated to 80° C. After 1 h, the reaction was cooled down to room temperature and treated with crushed ice. The mixture was then rendered basic using ammonium hydroxide. The aqueous mixture was extracted twice with dichloromethane. The organic layers were combined and washed with water and brine. The organic portion was dried with sodium sulfate, reduced in vacuo and placed on a vacuum line to give an oil. Yield=3.5 g. MS (M+H)+ 216.

Workup

  1. temperaturethe reaction was cooled down to room temperature
  2. additiontreated with crushed ice
  3. extractionThe aqueous mixture was extracted twice with dichloromethane
  4. washwashed with water and brine
  5. dry with materialThe organic portion was dried with sodium sulfate
  6. customto give an oil

Sources & evidence

ORD record
ord-7ff084d2d1294f349cc9e98222227c6f
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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