Aldoxime → HCID 86738776, compound

HRID 1757958Notes

Reaction equation

HRID 1757958 reaction equation
[H-].[Na+].C(=N[OH:6])C.[Cl:7][C:8]1[C:17]([Cl:18])=[C:16]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([N+]([O-])=O)=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:9]=1[O:10][CH:11]([OH:13])[CH3:12]>CN(C=O)C>[Cl:7][C:8]1[C:17]([Cl:18])=[C:16]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([OH:6])=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:9]=1[O:10][CH:11]([OH:13])[CH3:12]

Participants

5

Reactant 3

HCID 7863AldoximeHCID 24758Sodium hydrideHCID 86738777HCID 86738777, compound

Product 1

HCID 86738776HCID 86738776, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dry DMF (40 ml.) was cooled in an ice bath to 10°-15° C. Sodium hydride (7.2 g., 0.15 mole) was then added. The suspended mixture was stirred for 10 minutes and acetaldoxime (11.8 g., 0.2 mole) was added portionwise. After stirring for another 10 minutes the compound from Example 1 (17.8 g., 0.05 mole) in 30 ml. dry DMF was added dropwise. When the addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature for 21/2 hours. The mixture was poured into ice water and was filtered. The filtrate was acidified with concentrated HCl to obtain a precipitate. The crude solid was purified from aqueous ethanol to yield 11 g. (67%), m.p. 169°-170° C.

Workup

  1. additionWhen the addition
  2. customthe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 21/2 hours
  4. additionThe mixture was poured into ice water
  5. filtrationwas filtered
  6. customto obtain a precipitate
  7. customThe crude solid was purified from aqueous ethanol
  8. customto yield 11 g

Sources & evidence

ORD record
ord-a06ffd6e0742485395e52a495c0fdd8f
Source dataset
uspto-grants-1983_02
Patent number
US04371546

Reaction notes

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