Mercapto-ethanol → HCID 13363162, compound

HRID 1979996Notes

Reaction equation

HRID 1979996 reaction equation
CC(C)([O-])C.[K+].[SH:7][CH:8](O)[CH3:9].Br[CH2:12][CH2:13][C:14]1[C:15]2[N:16]([N:27]=[CH:28][N:29]=2)[C:17]([NH2:26])=[N:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)(C)(C)C>[CH2:8]([S:7][CH2:12][CH2:13][C:14]1[C:15]2[N:16]([N:27]=[CH:28][N:29]=2)[C:17]([NH2:26])=[N:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:9]

Participants

5

Reactant 3

HCID 4713212Mercapto-ethanolHCID 13363161HCID 13363161, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13363162HCID 13363162, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 1.08 g (9.7 mmole) of potassium t-butoxide in 30 ml of cold (circa 0°) t-butyl alcohol was added 0.8 g (12.9 mmole) of mercaptoethanol, and the mixture was allowed to warm to room temperature. The title compound of Example 19 (2.05 g, 6.4 mmole) was added and the mixture was heated at reflux for two hours. Upon cooling, the mixture was concentrated in vacuo and the residue was treated with 50 ml of water. The mixture was extracted with chloroform/dichloromethane and the organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated to dryness. Column chromatography of the crude product on silica gel afforded 350 mg of the title compound, m.p. 120°-122°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for two hours
  3. temperatureUpon cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. additionthe residue was treated with 50 ml of water
  6. extractionThe mixture was extracted with chloroform/dichloromethane
  7. washthe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f231f1018a9742688786accdf1cef337
Source dataset
uspto-grants-1984_11
Patent number
US04483987

Reaction notes

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