Sodium hydride → HCID 59168221, compound

HRID 1444022Notes

Reaction equation

HRID 1444022 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]([O:12][CH3:13])[C:7]([NH2:11])=[N:8][C:9]=1[CH3:10].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[S:22](Cl)(=[O:24])=[O:23].ClCCl.C(O)(=O)C>CN1CCCC1=O>[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[S:22]([NH:11][C:7]1[C:6]([O:12][CH3:13])=[N:5][C:4]([Br:3])=[C:9]([CH3:10])[N:8]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 21922555Acetic acid methylene chlorideHCID 59168136HCID 59168136, compound

Product 1

HCID 59168221HCID 59168221, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Sodium hydride (0.5 g of a 60% dispersion in oil) was added to a solution of 5-bromo-3-methoxy-6-methyl-2-pyrazinamine (Example 118c) (0.55 g) in N-methylpyrrolidinone (25 mL). The resultant dark solution was stirred at room temperature for 0.5 h before a solution of 2,3-dichlorobenzenesulphonyl chloride (0.67 g) in N-methylpyrrolidinone (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for 3 h, then quenched with aqueous ammonium chloride and partitioned between ethyl acetate and aqueous ammonium chloride (×5). the organic phase was dried (MgSO4), filtered and evaporated to give the crude product. Chromatography on silica gel eluting with dichloromethane/acetic acid (200:1) gave the title compound as a pale yellow solid (0.38 g).

Workup

  1. additionwas added dropwise
  2. customquenched with aqueous ammonium chloride
  3. custompartitioned between ethyl acetate and aqueous ammonium chloride (×5)
  4. dry with materialthe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product

Sources & evidence

ORD record
ord-3beaed8d48b2405ba928ff9061d39101
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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