Diethyl Ether → HCID 86736767, compound

HRID 2051779Notes

Reaction equation

HRID 2051779 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4](=[N:11][OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCOCC.[Cl:23][CH:24]([F:28])[C:25](Cl)=[O:26]>O>[Cl:23][CH:24]([F:28])[C:25]([NH:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4](=[N:11][OH:12])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:26]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 86654Methanone, (2-amino-5-chlorophenyl)phenyl-, oximeHCID 30138612-Chloro-2-fluoroacetyl chloride2×

Product 1

HCID 86736767HCID 86736767, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Water, 250 ml, was added to a solution of 50 g (0.203 mole) of 2-amino-5-chlorobenzophenone oxime (mixture of isomers) in 1 l. of ether, and the mixture was stirred rapidly and cooled to 5°. Solutions of (A) 100 ml of 10% sodium hydroxide in water and (B) 33.5 g (0.228 mole) of chlorofluoroacetyl chloride made up to 100 ml with ether were simultaneously added at the same rate over 30 min., keeping the temperature of the reaction mixture at about 10° with cooling. The reaction mixture was stirred for 30 min. after the addition, and the ether layer was separated, washed with water, dried (MgSO4), and evaporated to dryness under reduced pressure. The residue was recrystallized from benzene to give 61.2 g (88%) of 2-(chlorofluoroacetamido)-5-chlorobenzophenone oxime (mixture of isomers) as light yellow crystals, mp 110°-129°. The 19F nmr (acetone-d6) indicates a mixture of two isomers in a 70:30 ratio: δ -143.2 ppm (d, d, J=50, 2.5 Hz, 30%) and δ -144.3 ppm (d, d, J=50, 2.5 Hz, 70%).

Workup

  1. temperaturecooled to 5°
  2. additionwere simultaneously added at the same rate over 30 min.
  3. customat about 10°
  4. temperaturewith cooling
  5. additionafter the addition
  6. customthe ether layer was separated
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness under reduced pressure
  10. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-b9f8df283077471a837b39506b579364
Source dataset
uspto-grants-1980_01
Patent number
US04182760

Reaction notes

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