Ethanol → HCID 86759071, compound

HRID 1358166Notes

Reaction equation

HRID 1358166 reaction equation
[CH2:1]([C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=O)[C:5]=2[C:4]=1CC)[CH3:2].[Cl-].[OH:21][NH3+:22].O.[CH2:24](O)[CH3:25]>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:16]=[C:15]([CH2:24][CH3:25])[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[N:22][OH:21])[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 21645Hydroxylamine HClHCID 144535571,2-Diethyl-9H-thioxanthen-9-one

Product 1

HCID 86759071HCID 86759071, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

7.0 g (26 mmol) of diethylthioxanthen-9-one are dissolved in 15 ml of hot ethanol and 15 ml of pyridine. Then hydroxylammonium chloride (3.6 g, 52 mmol) is added, and the reaction solution is stirred at 115° C. for 21 h. After cooling, water is added. The crude product is extracted with ethyl acetate, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:30 to 1:10) as an eluent. The product (an isomeric mixture) is obtained as a slightly yellow solid. 1H NMR (CDCl3), δ[ppm]: 1.23-1.32 (m, 6H), 2.65-2.72 (m, 2H), 2.77-2.86 (m, 2H), 7.12(s, 1H), 7.30-7.36 (m, 2H), 7.45 (dd, 1/2H), 7.53-7.55 (m, 1H), 7.80 (dd, 1/2H), 8.03 Cd, 1/2H), 8.09-8.48 (bs, 1H), 8.34 (dd, 1/2H), wherein 1/2H means 1H of either isomer.

Workup

  1. temperatureAfter cooling
  2. extractionThe crude product is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:30 to 1:10) as an eluent
  7. customThe product (an isomeric mixture) is obtained as a slightly yellow solid

Sources & evidence

ORD record
ord-a8be16e88dcf452c8d9d325ed64b18e1
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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