4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride → HCID 178497579, compound

HRID 1517383Notes

Reaction equation

HRID 1517383 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[S:11](Cl)(=[O:13])=[O:12].[CH3:15][NH:16][CH2:17][C:18]1[NH:22][C:21]2[C:23]([C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]=1>C(Cl)Cl>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([S:11]([N:16]([CH2:17][C:18]2[NH:22][C:21]3[C:23]([C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=[CH:26][C:20]=3[N:19]=2)[CH3:15])(=[O:13])=[O:12])=[C:4]([CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 178483008HCID 178483008, compound

Product 1

HCID 178497579HCID 178497579, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2,6-dimethyl-4-methoxybenzenesulfonyl chloride (12.54 mmol, 1.0 eq.) in methylene chloride (12 ml) was added to a cooled solution (0° C.) of methyl 2-((methylamino)methyl)-1H-benzo[d]imidazole-7-carboxylate (12.54 mmol, 1.0 eq.) and TEA (2.5 eq.) in abs. methylene chloride (60 ml). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with methylene chloride and washed successively with water and sat. NaCl solution. The organic phase was dried over Na2SO4 and the solvent was evaporated off in vacuo to obtain the crude product, which led to the desired product by purification by column chromatography (silica gel). Yield: 46%

Workup

  1. washwashed successively with water and sat. NaCl solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated off in vacuo

Sources & evidence

ORD record
ord-bcf52f204ed1430ba2dcaef4e463f15c
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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