Water → HCID 85885610, compound

HRID 1709984Notes

Reaction equation

HRID 1709984 reaction equation
O[C:2]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:5].[H-].[Na+].C(OC(=O)CCCCBr)C.O>CN(C)C=O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[C:15]([O:18][CH2:19][C:20]([F:22])([F:23])[F:21])[CH:16]=[CH:17][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 15055922HCID 15055922, compound

Product 1

HCID 85885610HCID 85885610, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, 3.5 g of 60% sodium hydride in mineral oil is washed twice with hexane and then suspended in 80 ml of dry dimethylformamide. A solution of 22.5 g (0.069 mole) of 2-hydroxy-N-(2-pyridylmethyl)-5-(2,2,2-trifluoroethoxy)benzamide in 100 ml of dimethylformamide is added dropwise to the sodium hydride suspension to give a thick foam. After the addition is complete the reaction mixture is stirred for 30 minutes at about 25° C. and for another 30 minutes at about 60° C. A solution of 20.2 g (0.097 mole) of 5-bromovaleric acid ethyl ester in 40 ml of dimethylformamide is added dropwise with stirring to the reaction mixture. The resulting pale brown solution is allowed to stir at about 60° C. for about 16 hours. The solution is poured into about 1 liter of cold water and then chilled. The resulting precipitate is collected, rinsed with cold water and then dissolved in chloroform. The chloroform solution is washed through a short Florisil® column and the eluent is evaporated to give 28.3 g of an ivory, waxy solid. This material is recrystallized from about 280 ml of 2:1 ethanol:water to give 23.1 g of ivory crystalline 2-(4-ethoxycarbonyl-butoxy(-N-(2-pyridylmethyl)-5-(2,2,2-trifluoroethoxy)benzamide, m.p. 88°-90° C.

Workup

  1. washUnder a nitrogen atmosphere, 3.5 g of 60% sodium hydride in mineral oil is washed twice with hexane
  2. customto give a thick foam
  3. additionAfter the addition
  4. stirringwith stirring to the reaction mixture
  5. stirringto stir at about 60° C. for about 16 hours
  6. temperaturechilled
  7. customThe resulting precipitate is collected
  8. washrinsed with cold water
  9. dissolutiondissolved in chloroform
  10. washThe chloroform solution is washed through a short Florisil® column
  11. customthe eluent is evaporated
  12. customto give 28.3 g of an ivory, waxy solid
  13. customThis material is recrystallized from about 280 ml of 2:1 ethanol

Sources & evidence

ORD record
ord-b0fdb31ce4ca4ec19d966d20035b4b78
Source dataset
uspto-grants-1990_08
Patent number
US04952574

Reaction notes

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