Water → HCID 53908529, compound

HRID 1156727Notes

Reaction equation

HRID 1156727 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[H-].[Na+].[CH3:24]I.O>CN(P(N(C)C)(N(C)C)=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH3:24])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13318567HCID 13318567, compound

Product 1

HCID 53908529HCID 53908529, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 3.1 g 3-(4-chloro-2-nitrophenylamino)-pyrazine-2-carboxylic acid methyl ester in 15 ml absolute hexamethylphosphorotriamide is treated portionwise with 0.3 g sodium hydride. The reaction mixture is stirred at room temperature for 1 hour and then treated dropwise with 2.8 g methyl iodide, and the temperature is maintained under 20° C. After the reaction mixture has been stirred for 1 hour at room temperature 10 ml water are added dropwise. The mixture is extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and evaporated. The residue is recrystallised from ethyl acetate to give the heading compound, m.p. 111°-112°.

Workup

  1. temperaturethe temperature is maintained under 20° C
  2. additionare added dropwise
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue is recrystallised from ethyl acetate
  8. customto give the heading compound, m.p. 111°-112°

Sources & evidence

ORD record
ord-207501a20c874efea781d4a8318a874d
Source dataset
uspto-grants-1982_06
Patent number
US04337198

Reaction notes

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