Sodium Iodide → HCID 23035294, compound

HRID 1709991Notes

Reaction equation

HRID 1709991 reaction equation
[OH:1][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+].[I-].[Na+].Cl[CH2:29][C:30]([NH2:32])=[O:31]>CN(C)C=O.O>[C:30]([CH2:29][O:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:21])[F:22])=[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])(=[O:31])[NH2:32]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6580ChloroacetamideHCID 24758Sodium hydrideHCID 15055922HCID 15055922, compound

Product 1

HCID 23035294HCID 23035294, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of 6.5 g (0.02 mole) of 2-hydroxy-N-(2-pyridylmethyl)-5-(2,2,2-trifluoroethoxy)benzamide in 20 ml of dimethylformamide was added dropwise to a suspension of 0.021 mole of sodium hydride in 10 ml dimethylformamide. The resulting mixture was stirred at about 25° C. for 30 minutes, at 60° C. for 30 minutes, and then 0.3 g of sodium iodide was added followed by the addition of a solution of 1.7 g (0.018 mole) of 2-chloroacetamide in 15 ml dry dimethylformamide. The reaction mixture was stirred for about 16 hours at 60° C. and then poured into 500 ml cold water. The resulting precipitate was collected and dried, then dissolved in a minimum of 5% methanol in chloroform and washed through a column of basic alumina. The eluent was evaporated to give a white solid which was recrystallized from about 300 ml of 3:4 water:ethanol to give 4.9 g of white crystalline 2-carbamoylmethoxy-N-(2-pyridylmethyl)-5-(2,2,2-trifluoroethoxy)benzamide.

Workup

  1. stirringThe reaction mixture was stirred for about 16 hours at 60° C.
  2. customThe resulting precipitate was collected
  3. customdried
  4. dissolutiondissolved in a minimum of 5% methanol in chloroform
  5. washwashed through a column of basic alumina
  6. customThe eluent was evaporated
  7. customto give a white solid which
  8. customwas recrystallized from about 300 ml of 3:4 water

Sources & evidence

ORD record
ord-42455b64ef1f4df3a8f3a74ad3af3cc9
Source dataset
uspto-grants-1990_08
Patent number
US04952574

Reaction notes

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