Potassium hydroxy sulfite → HCID 54671266, compound

HRID 449307Notes

Reaction equation

HRID 449307 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[N:16]=[C:15]3[N:17]([CH2:20][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)[N:18]=[N:19][C:14]3=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH:31]OS([O-])=O.[K+]>CC(C)=O.O.C(=O)(O)[O-].[Na+]>[C:4]([C:3]1[CH:7]=[CH:8][C:9]([C:11]2[N:16]=[C:15]3[N:17]([CH2:20][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N+:27]([O-:31])=[CH:26][CH:25]=[CH:24]5)[N:18]=[N:19][C:14]3=[CH:13][CH:12]=2)=[CH:10][C:2]=1[Cl:1])(=[O:5])[NH2:6]

Participants

6

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 58514760HCID 58514760, compound

Product 1

HCID 54671266HCID 54671266, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of example 108 (0.100 g, 0.241 mmol) in acetone (0.6 ml), oxone (0.74 g, 1.20 mmol) in water (2 ml) was added and heated under reflux for 20 h. The mixture was diluted with aqueous 10% sodium bicarbonate solution and extracted with dichloromethane, the organic layer dried over anhydrous sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound (0.030 g, 29%) as a pale brown solid. M.P.: 182-183° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.71 (d, J=8.8 Hz, 1H), 8.55 (d, J=6.1 Hz, 1H), 8.52 (d, J=9.1 Hz, 1H), 8.29 (s, 1H), 8.23 (m, 2H), 8.12 (s, 1H), 7.95-7.83 (m, 3H), 7.67 (s, 1H), 7.61 (d, J=7.9 Hz, 1H), 7.47 (dd, J=8.4, 6.2 Hz, 1H), 6.24 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 h
  3. extractionextracted with dichloromethane
  4. dry with materialthe organic layer dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-2574e61fbc9c495e9b94eaabd8df31f9
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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