Potassium Carbonate → 10-Hexyl-3,7-dimethoxy-phenothiazine

HRID 2395133Notes

Reaction equation

HRID 2395133 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][CH:9]=3.C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(OCC)(=O)C.CCCCCC>[CH2:26]([N:7]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([O:17][CH3:18])[CH:12]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 6211963,7-Dimethoxy-10H-phenothiazine

Product 1

HCID 1897249610-Hexyl-3,7-dimethoxy-phenothiazine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A suspension of 15.0 g (57.8 mmol) of 3,7-dimethoxyphenothiazine, 31.9 g (0.231 mmol) of powdered potassium carbonate, 61.29 g (0.289 mol) of 1 -iodohexane and 1.6 g (5.0 mmol) of tris-[2-(2-methoxymethoxy)ethyl]amine was heated to 110° for 64 hours. The working up was effected analogously to that described in Example 4.1.1.b. After chromatography on silica gel with ethyl acetate/hexane (1:4) 18.33 g (91.8%) of 10-hexyl-3,7-dimethoxy-phenothiazine were obtained as a brownish oil.

Workup

  1. temperaturewas heated to 110° for 64 hours

Sources & evidence

ORD record
ord-409a7d19924f4574a0b323b26b83a1fc
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

Loading…