Water → HCID 21409981, compound

HRID 1658611Notes

Reaction equation

HRID 1658611 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[O:11])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:30][CH2:31][C:32](Br)=[O:33].O>C(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][N:7]([C:8]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[O:11])[C:32](=[O:33])[CH2:31][Br:30])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 21409977HCID 21409977, compound

Product 1

HCID 21409981HCID 21409981, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2.5g (0.0074 M) of 2-(2-acetoxyethylamino)-5-chloro-2'-flurobenzophenone and 5g (0.0362 M) of potassium carbonate in 25 ml of dry chloroform was treated with 2.0g (0.0096 M) of bromoacetyl bromide over a 20 minute period with stirring. The mixture was stirred for 1 hour at room temperature when 25 ml of water was added, and the chloroform layer was separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residual oil was dissolved in 10 ml of benzene, and chromatographed over 100g of Florisil. Elution with 1 l. of benzene gave 0.2g of an oil and elution with 1.5 l. of ether and 1 l. of ethyl acetate gave 1.8g and 1.0g, respectively of a colorless oil which were combined and recrystallized from a mixture of dichloromethane and petroluem ether to give the above named product as white prisms, m.p. 84°-88°.

Workup

  1. additionwas added
  2. customthe chloroform layer was separated
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. dissolutionThe residual oil was dissolved in 10 ml of benzene
  7. customchromatographed over 100g of Florisil
  8. washElution with 1 l
  9. customof benzene gave
  10. wash0.2g of an oil and elution with 1.5 l
  11. customof ethyl acetate gave 1.8g and 1.0g
  12. customrecrystallized from a mixture of dichloromethane and petroluem ether
  13. customto give the above named product as white prisms, m.p. 84°-88°

Sources & evidence

ORD record
ord-c83bfd38bae042f5bee5c14fc2d099ca
Source dataset
uspto-grants-1976_06
Patent number
US03965151

Reaction notes

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