Ammonia → HCID 18670652, compound

HRID 1059307Notes

Reaction equation

HRID 1059307 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([S:13][C:14]2[C:15](Cl)=[N:16][CH:17]=[CH:18][N:19]=2)[C:10]([N+:21]([O-])=O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Na].N>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]2[NH:21][C:15]3[N:16]=[CH:17][CH:18]=[N:19][C:14]=3[S:13][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 18670174HCID 18670174, compound

Product 1

HCID 18670652HCID 18670652, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.7 g of methyl 2-methoxy-4-(2-chloropyrazin-3-yl)thio-5-nitrobenzoate in tetrahydrofuran (100 ml) were added 50 ml of a saturated aqueous solution of sodium hydrosufide and 30 ml of 27% aqueous ammonia and the resulting mixture was vigorously stirred at room temperature for 1 hour. Then the reaction mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, a solution of the residue in tetrahydrofuran was stirred at 70° C. for 1 hour. After distilling off the solvent under reduced pressure, dichloroemthane was added to the residue. The crystals thus precipitated were filtered to thereby give 1.9 g of the title compound as red crystals.

Workup

  1. extractionThen the reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent under reduced pressure
  4. stirringa solution of the residue in tetrahydrofuran was stirred at 70° C. for 1 hour
  5. distillationAfter distilling off the solvent under reduced pressure, dichloroemthane
  6. additionwas added to the residue
  7. customThe crystals thus precipitated
  8. filtrationwere filtered

Sources & evidence

ORD record
ord-1e364d11221b4d058e25dafcb9c1dc8e
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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