Water → 1-phenothiazin-10-ylpropan-2-ol

HRID 1032961Notes

Reaction equation

HRID 1032961 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].[CH2:17]1[O:20][CH:18]1[CH3:19].O>C1(C)C(C)=CC=CC=1>[OH:20][CH:18]([CH3:19])[CH2:17][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6378Propylene OxideHCID 7108PhenothiazineHCID 24533Sodium amide

Product 1

HCID 3775581-phenothiazin-10-ylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of phenothiazine (5 g, 25.1 mmol) and sodium amide (95%, 1.2 g, 29 mmol) in xylene (30 ml) was heated under reflux for 3 hours. Then propylene oxide (2.5 ml, 37 mmol) was added thereto under ice-cooling, and the reaction mixture was heated under reflux for 3 hours. To the reaction mixture was added water, and the mixture was extracted with chloroform, washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The thus-obtained black-brown solution containing xylene was purified by column chromatography on silica gel to give a dark black oil. Yield 4.19 g (65%).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureunder ice-cooling
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 3 hours
  5. extractionthe mixture was extracted with chloroform
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. additionThe thus-obtained black-brown solution containing xylene
  10. customwas purified by column chromatography on silica gel
  11. customto give a dark black oil

Sources & evidence

ORD record
ord-18d02cc608b347de822620beee99eaf4
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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