Sodium hydride → HCID 59168195, compound

HRID 1444028Notes

Reaction equation

HRID 1444028 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[N:21][CH:20]=[CH:19][N:18]=1)=[O:16].[H-].[Na+]>O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:23][C:22]1[C:17]([C:15]([O:14][CH3:13])=[O:16])=[N:18][CH:19]=[CH:20][N:21]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 27342222,3-Dichlorobenzene-1-sulfonyl chloride

Product 1

HCID 59168195HCID 59168195, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2,3-dichlorobenzenesulphonyl chloride (0.246 g) and methyl-3-aminopyrazine-2-carboxylate (0.153 g) in 1,2-dimethoxymethane (3 mL) was added portionwise sodium hydride (0.1 g of a 60% dispersion in oil) over 1 hour. The mixture was stirred at room temperature for 20 h, was poured into water (20 mL) and extracted into ethyl acetate (2×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated to afford an oil that was purified by chromatography on silica gel eluting with dichloromethane to afford the titled compound (0.085 g) as a white solid.

Workup

  1. extractionextracted into ethyl acetate (2×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford an oil that
  6. customwas purified by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-27f33920867b421b82e393578fd8508b
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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