Cornforth reagent → HCID 54481624, compound

HRID 964452Notes

Reaction equation

HRID 964452 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:21]2[CH:20]=[C:19]([C:22](=[O:24])[CH3:23])[CH:18]=[CH:17][C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:26].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O.CCOCC>[C:22]([C:19]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:26])=[O:1])[C:21]=2[CH:20]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 70131253HCID 70131253, compound

Product 1

HCID 54481624HCID 54481624, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 41 mg (0.12 mmol) of 1-[10-(6-hydroxyhexyl)-10H-phenothiazin-2-yl]ethanone in 0.16 mL of N,N-dimethylformamide is treated with 158 mg (0.42 mmol) of pyridinium dichromate and stirred at room temperature for 12 hours. The mixture is diluted with ether and filtered through a pad of celite with the aid of 100 mL of ether. The filtrate is washed successively with 10% sodium bisulfate solution and saturated sodium chloride solution, then dried over magnesium sulfate and concentrated in vacuo to give 10 mg (23%) of 2-acetyl-10H-phenothiazine-10-hexanoic acid as a dark residue. The 1 H NMR (300 MHz, CDCl3) is consistent with the desired product. MS (CI) m/e 323 (M+ +H).

Workup

  1. filtrationfiltered through a pad of celite with the aid of 100 mL of ether
  2. washThe filtrate is washed successively with 10% sodium bisulfate solution and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77d48aa02f074873af3d8588fb30e5ff
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

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