Water → HCID 21409981, compound

HRID 328501Notes

Reaction equation

HRID 328501 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'-fluorobenzophenone 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 anhhydrous 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 petroleum 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 anhhydrous 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 petroleum ether
  13. customto give the above named product as white prisms, m.p. 84°-88°

Sources & evidence

ORD record
ord-8f1fb5a9a0c24ab180526de74415c5a3
Source dataset
uspto-grants-1977_04
Patent number
US04017532

Reaction notes

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