Water → Di-(4-chlorophenyl)methyleneamino-oxyacetamide

HRID 47081

Reaction equation

HRID 47081 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([C:8](=[N:16][OH:17])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.Cl[CH2:21][C:22]([NH2:24])=[O:23].O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8](=[N:16][O:17][CH2:21][C:22]([NH2:24])=[O:23])[C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6580ChloroacetamideHCID 24758Sodium hydrideHCID 743894,4'-Dichlorobenzophenone oxime

Product 1

HCID 12942464Di-(4-chlorophenyl)methyleneamino-oxyacetamideYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.5 g., 50% w/w suspension in mineral oil) was added gradually to a stirred solution of 4,4'-dichlorobenzophenone oxime (2.6 g.) in dry dimethylformamide (20 ml.) keeping the temperature below 30° C. After 30 minutes, chloroacetamide (0.9 g.) was added to the stirred solution keeping the temperature below 30° C. After 16 hours stirring at ambient temperature the mixture was poured into water (100 ml.) and the subsequent mixture extracted with ether. The combined extract was washed with water, dried (MgSO4) and evaporated. The residue (2.5 g.) was added to a column of dry chromatographic silica-gel [300 g., previously deactivated by addition of 10% w/w water and then equilibrated with 10% v/w of a mixture of toluene and acetone (10:1 v/w)]. The column was then eluted with the same mixture of toluene and acetone to give, after evaporation of solvent, a solid residue (1.5 g.). The solid was recrystallised from ethyl acetate/petrol giving di-(4-chlorophenyl)methyleneamino-oxyacetamide m.p. 141°-142° C. (1.1 g.) in 34% overall yield.

Workup

  1. customthe temperature below 30° C
  2. customthe temperature below 30° C
  3. extractionthe subsequent mixture extracted with ether
  4. extractionThe combined extract
  5. washwas washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. additionThe residue (2.5 g.) was added to a column of dry chromatographic silica-gel [300 g
  9. addition, previously deactivated by addition of 10% w/w water
  10. additionequilibrated with 10% v/w of a mixture of toluene and acetone (10:1 v/w)]
  11. washThe column was then eluted with the same mixture of toluene and acetone
  12. customto give
  13. customafter evaporation of solvent
  14. customThe solid was recrystallised from ethyl acetate/petrol

Sources & evidence

ORD record
ord-4be65f9271554c169cb8663e62cfe682
Source dataset
uspto-grants-1979_11
Patent number
US04176194

Linked notes

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