HCID 2766, compound → HCID 136171397, compound

HRID 978069Notes

Reaction equation

HRID 978069 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([OH:17])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=O)[CH:7]=1.[NH2:19][CH2:20][CH:21]=[CH:22][C:23]([OH:25])=[O:24].C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([OH:17])=[C:6]([C:8](=[N:19][CH:20]=[CH:21][CH2:22][C:23]([OH:25])=[O:24])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 2766HCID 2766, compoundHCID 516892Sodium BicarbonateHCID 30211374',5-Dichloro-2-hydroxy-3-methylbenzophenone

Product 1

HCID 136171397HCID 136171397, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 1-l round-bottomed flask, 15.3 g (0.054 mole) of (5-chloro-2-hydroxy-3-methylphenyl)(4-chlorophenyl)methanone, 5 g (0.049 mole) of 4-amino-2-butenoic acid and 4.5 g (0.054 mole) of sodium hydrogencarbonate are introduced in 700 ml of methanol. The mixture is evaporated to dryness on a water bath at 100° C. under reduced pressure. The operation is repeated seven times, evaporating 500 ml of methanol at a time. The dry residue is taken up with 200 ml of methylene chloride and 300 ml of water, acidified to pH 4 with 3.7 g of citric acid and then extracted with l of methylene chloride. The organic phase is washed with water, decanted, dried over MgSO4, filtered and evaporated to dryness. The compound is crystallised in 100 ml of hexane, filtered, drained and dissolved in 100 ml of ethyl acetate. The product crystallises slowly. It is filtered, drained and washed with 10 ml of ether.

Workup

  1. customThe mixture is evaporated to dryness on a water bath at 100° C. under reduced pressure
  2. customevaporating 500 ml of methanol at a time
  3. extractionextracted with l of methylene chloride
  4. washThe organic phase is washed with water
  5. customdecanted
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe compound is crystallised in 100 ml of hexane
  10. filtrationfiltered
  11. dissolutiondissolved in 100 ml of ethyl acetate
  12. customThe product crystallises slowly
  13. filtrationIt is filtered
  14. washwashed with 10 ml of ether

Sources & evidence

ORD record
ord-9f0193f73da74abb99a1a9e5d6732980
Source dataset
uspto-grants-1987_05
Patent number
US04663350

Reaction notes

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