Ethanesulfonylchloride, 2-chloro- → HCID 711232, compound

HRID 1622574Notes

Reaction equation

HRID 1622574 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]([C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=[CH:8][N:9]=1.Cl[CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18].C(=O)([O-])O.[Na+]>C1COCC1>[N:3]1[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=12

Participants

6

Reactant 4

HCID 15385Ethanesulfonylchloride, 2-chloro-3×HCID 24758Sodium hydrideHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 711232HCID 711232, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60%, 2.0 g) in dry THF (100 mL) were added under ice-cooling methyl 3-aminopyrazine-2-carboxylate (1.53 g) and, 2-chloroethanesulfonyl chloride (2.1 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2-chloroethanesulfonyl chloride (2.1 mL), and the mixture was stirred at room temperature for 3 days. 2-Chloroethanesulfonyl chloride (2.1 mL) was added, and the mixture was stirred at room temperature for 3 days. The reaction mixture was added dropwise to aqueous sodium hydrogen carbonate (15.1 g) solution (400 mL) under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. The precipitated was collected by filtration, washed successively with water and a small amount of methanol, and dried to give the title compound (1.62 g) as a pale-yellow solid.

Workup

  1. additionwere added under ice-
  2. stirringthe mixture was stirred at room temperature for 3 days
  3. stirringthe mixture was stirred at room temperature for 3 days
  4. temperaturecooling
  5. stirringthe mixture was stirred at the same temperature for 1 hr
  6. filtrationThe precipitated was collected by filtration
  7. washwashed successively with water
  8. dry with materiala small amount of methanol, and dried

Sources & evidence

ORD record
ord-d657d8a3eb3b4e638f6f542f99851fea
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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