O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamine → HCID 136127206, compound

HRID 1761803Notes

Reaction equation

HRID 1761803 reaction equation
[C:1]([C:4]1[C:5](=[O:17])[CH2:6][CH:7]([CH:11]2[CH2:16][CH2:15][CH2:14][S:13][CH2:12]2)[CH2:8][C:9]=1[OH:10])(=O)[CH3:2].[Cl:18][C:19]1[S:23][C:22]([CH2:24][O:25][NH2:26])=[CH:21][CH:20]=1>C(O)C>[Cl:18][C:19]1[S:23][C:22]([CH2:24][O:25][N:26]=[C:1]([C:4]2[C:5](=[O:17])[CH2:6][CH:7]([CH:11]3[CH2:16][CH2:15][CH2:14][S:13][CH2:12]3)[CH2:8][C:9]=2[OH:10])[CH3:2])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 10986580O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamineHCID 15614621HCID 15614621, compound

Product 1

HCID 136127206HCID 136127206, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution containing 5.1 g (0.020 mol) of 2-acetyl-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)cyclohex-2-en-1-one and 3.4 g (0.021 mol) of (5-chlorothien-2-yl)methoxyamine in 200 ml of ethanol was stirred overnight (about 14 hours) at room temprature and then evaporated to remove ethanol. The concentrate was diluted with 150 ml of methylene chloride and then washed with 100 ml of water and then with 100 ml of saturated aqueous sodium chloride solution. The washed methylene chloride solution was dried over anhydrous magnesium sulfate and then evaporated to dryness under reduced pressure to afford a white solid. Recrystallation of this solid absolute ethanol afforded 7.6 g of the title compound, m.p. 154°-155° C.

Workup

  1. customevaporated
  2. customto remove ethanol
  3. additionThe concentrate was diluted with 150 ml of methylene chloride
  4. washwashed with 100 ml of water
  5. dry with materialThe washed methylene chloride solution was dried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customto afford a white solid

Sources & evidence

ORD record
ord-2ce1995f75d54ea3840fee27d589ec9f
Source dataset
uspto-grants-1989_05
Patent number
US04828601

Reaction notes

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