Sodium Hydroxide → HCID 13055746, compound

HRID 647464Notes

Reaction equation

HRID 647464 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[N:8]([CH3:21])[C:9](=[O:20])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)Cl.[OH-].[Na+]>CC(O)C>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C@@H:10]2[C:9](=[O:20])[N:8]([CH3:21])[C@H:3]3[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]3[O:1]2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13055743HCID 13055743, compound

Product 1

HCID 13055746HCID 13055746, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The crude chloroacetamide (3.1 g) was dissolved in propan-2-ol (30 cm3) and treated with 10 N sodium hydroxide solution (3 cm3). The mixture was stirred at room temperature for 5 hrs. and was left overnight. The phases were separated and the organic phase was concentrated under reduced pressure. The residue was dissolved in ether-dichloromethane (1:1 v/v, 70 cm3) and washed with the alkaline phase diluted with water. The aqueous phase was extracted with dichloromethane (2×30 cm3). The combined organic phases were washed with saturated brine, dried (Na2SO4), and evaporated, leaving crude mixture of the title compounds as a brown oil (2.11 g).

Workup

  1. waitand was left overnight
  2. customThe phases were separated
  3. concentrationthe organic phase was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ether-dichloromethane (1:1 v/v, 70 cm3)
  5. washwashed with the alkaline phase
  6. additiondiluted with water
  7. extractionThe aqueous phase was extracted with dichloromethane (2×30 cm3)
  8. washThe combined organic phases were washed with saturated brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customleaving crude

Sources & evidence

ORD record
ord-42ccda1fd42048f78be007cce3542a80
Source dataset
uspto-grants-1983_10
Patent number
US04409218

Reaction notes

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