Water → HCID 70540935, compound

HRID 1702761Notes

Reaction equation

HRID 1702761 reaction equation
[CH2:1]([N:3]([C@@H:8]1[CH2:14][CH2:13][CH2:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[C@H:9]1[OH:19])[C:4](=[O:7])[CH2:5]Cl)[CH3:2].[H-].[Na+].O>CN(C)C=O>[CH2:1]([N:3]1[C:4](=[O:7])[CH2:5][O:19][C@@H:9]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[CH2:12][CH2:13][CH2:14][C@@H:8]12)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydride2×HCID 70474738HCID 70474738, compound

Product 1

HCID 70540935HCID 70540935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The residue from Step A was dissolved in 50 ml of dimethyl formamide and added dropwise to a solution of 0.7 g (0.0146 m) of a 50% oil dispersion of sodium hydride in 50 ml of dimethyl formamide with stirring. After stirring one hour, excess sodium hydride was decomposed by the addition of water. The mixture was extracted twice with ethyl acetate and the extract was back washed with water, dilute, cold hydrochloric acid and saturated aqueous sodium bicarbonate solution. After drying (Na2SO4) the ethyl acetate solution was concentrated to dryness in vacuo to provide crude product.

Workup

  1. stirringAfter stirring one hour
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washthe extract was back washed with water
  4. additiondilute
  5. dry with materialAfter drying (Na2SO4) the ethyl acetate solution
  6. concentrationwas concentrated to dryness in vacuo
  7. customto provide crude product

Sources & evidence

ORD record
ord-a98cd0a5e5d64ed6b4af0a8e39748adf
Source dataset
uspto-grants-1982_09
Patent number
US04349548

Reaction notes

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