Sulfuric Acid → Ethanol, 2-[2-(10H-phenothiazin-10-yl)ethoxy]-

HRID 2226739Notes

Reaction equation

HRID 2226739 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2.CC(O)C.S(=O)(=O)(O)O.[OH-].[Na+]>O>[CH:25]1[C:26]2[N:13]([CH2:12][CH2:11][O:10][CH2:9][CH2:8][OH:7])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:20][C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 18965314HCID 18965314, compound

Product 1

HCID 11822299Ethanol, 2-[2-(10H-phenothiazin-10-yl)ethoxy]-Yield 52.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of crude 10-(2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethyl)-10H-phenothiazine (3.8 g, 10 mmol), 2-propanol (50 ml) and a 4 M aqueous sulfuric acid solution (8 ml) was heated at 60° C. for 3 h and then left overnight at room temperature. The reaction mixture was poured into a mixture of water (500 ml) and a 4 N sodium hydroxide solution (17 ml). The mixture was extracted with diethyl ether (150 ml) and the organic extract was washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo to give 1.5 g of crude 2-(2-(10H-phenothiazin-10-yl)ethoxy)ethanol. TLC: rf=0.52 (SiO2 ; dichloromethane/methanol=19:1).

Workup

  1. extractionThe mixture was extracted with diethyl ether (150 ml)
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3887336a9a3f46b2a6c294d7d686288f
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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