5-Bromo-2-methyl-1H-benzo[d]imidazole → HCID 58107460, compound

HRID 873664Notes

Reaction equation

HRID 873664 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[NH:7][C:6]=2[CH:11]=1.C([Li])(C)(C)C.[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([C:22](N(OC)C)=[O:23])=[CH:20][C:19]=1[S:30](=[O:33])(=[O:32])[NH2:31]>O1CCCC1>[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([C:22]([C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[C:8]([CH3:10])[NH:7][C:6]=3[CH:11]=2)=[O:23])=[CH:20][C:19]=1[S:30]([NH2:31])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 6109795-Bromo-2-methyl-1H-benzo[d]imidazoleHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 58107460HCID 58107460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.303 g of 6-bromo-2-methyl-1H-benzoimidazole in tetrahydrofuran (20 mL) is cooled to −50° C. and treated with 2.7 mL of tert-butyllithium (1.5 M in pentane). After 2 h at −50° C. the reaction mixture is treated with 0.12 g of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide in tetrahydrofuran (10 mL). After 3 h the mixture is quenched with saturated aqueous ammonium chloride, taken up in ethyl acetate, and washed with saturated aqueous sodium chloride. The organics are dried (magnesium sulfate), concentrated and purified by silica gel chromatography (98:2 methylene chloride/methanol) to give 2-chloro-5-(2-methyl-3H-benzoimidazole-5-carbonyl)-benzenesulfonamide. MS (m/z): 348 (M−1); Rf 0.30 (9:1 methylene chloride/methanol).

Workup

  1. customAfter 3 h the mixture is quenched with saturated aqueous ammonium chloride
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialThe organics are dried (magnesium sulfate)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (98:2 methylene chloride/methanol)

Sources & evidence

ORD record
ord-8341fc17a26b4d9ca2143b996f11b4ea
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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