Diethyl Ether → HCID 54287253, compound

HRID 1578399Notes

Reaction equation

HRID 1578399 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC>O>[CH2:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:13])=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7057657HCID 7057657, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54287253HCID 54287253, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Twenty-three grams of trans-N-(2-ACETAMIDOCYCLOHEXYL)-p-TOLUENESULFONAMIDE was added in portions to a stirred suspension of 7 grams of lithium aluminium hydride and 500ml of anhydrous ether. The mixture was stirred and refluxed for 17 hours. The mixture was decomposed by dropwise addition of water and filtered. The filter cake was extracted with a total of 750 ml of boiling ethyl acetate. The organic portions were combined, dried over magnesium sulfate, then evaporated to dryness. The residue was slurried with ether and filtered. On recrystallization from ether there was obtained trans N-(2-ETHYLAMINOCYCLOHEXYL)-p-TOLUENESULFONAMIDE, mp. 112-4°C.

Workup

  1. temperaturerefluxed for 17 hours
  2. filtrationfiltered
  3. extractionThe filter cake was extracted with a total of 750 ml of boiling ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. filtrationfiltered
  7. customOn recrystallization from ether

Sources & evidence

ORD record
ord-5eaea857bb4c49488125a80f8679be18
Source dataset
uspto-grants-1976_02
Patent number
US03936471

Reaction notes

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