Methyl phenothiazin-2-yl ketone → HCID 70130690, compound

HRID 1417786Notes

Reaction equation

HRID 1417786 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].CCCCCC.C(OCC)(=O)C>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:41][C:39]([Si:36]([CH3:37])([CH3:38])[O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][N:7]1[C:6]2[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)([CH3:40])[CH3:42]

Participants

8

Reactant 4

HCID 81131Methyl phenothiazin-2-yl ketoneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 70130690HCID 70130690, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg (2.07 mmol) of 2-acetylphenothiazine in 8 mL of tetrahydrofuran is cooled to -78° C. and 4.14 mL (2.07 mmol) of a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene is added. After five minutes, a solution of [(6-bromohexyl)oxy]-(1,1-dimethylethyl)dimethyl silane in 2 mL of tetrahydrofuran is added and the reaction is allowed to warm to room temperature. The mixture is diluted with 25 mL of ethyl acetate and washed with 10% sodium bisulfate solution and saturated sodium chloride solution, then dried over magnesium sulfate and concentrated in vacuo to give a dark colored residue. Flash chromatography (3:1 hexane/ethyl acetate) provides 318 mg (33%) of 1-[10-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-10H-phenothiazin-2-yl]ethanone as a dark colored oil. The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 1680, 1600, 1560 cm-1 ; MS m/e calculated for C26H37NO2SSi: 455.2314, found 455.2312.

Workup

  1. washwashed with 10% sodium bisulfate solution and saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a dark colored residue

Sources & evidence

ORD record
ord-e5ad1c4f61a946908e2be60e7585c88d
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

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