Methane → 5-Chloro-2-[(2-methylphenyl)methyl]-1H-benzimidazole-6-sulfonamide

HRID 904852

Reaction equation

HRID 904852 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[C:8]([Cl:10])[C:7]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:6][C:4]=1[NH2:5].[CH3:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[CH2:18][C:19]#N.C>CO>[Cl:10][C:8]1[C:7]([S:11](=[O:13])(=[O:14])[NH2:12])=[CH:6][C:4]2[NH:5][C:19]([CH2:18][C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[CH3:15])=[N:2][C:3]=2[CH:9]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 311552-(o-Tolyl)acetonitrileHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897105-Chloro-2-[(2-methylphenyl)methyl]-1H-benzimidazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 50 ml of 6 N hydrochloric acid was added 11.8 g of 2-amino-4-chloro-5-sulfamylaniline and 10.4 g of 2-methylbenzyl cyanide. The reaction was refluxed for 22 hours and then concentrated in vacuo to a solid which was then added with stirring to 200 ml of 38% ammonium hydroxide. Filtration provided the free base as a semi-gum which was dissolved in 500 ml of methanol. The methanol solution was brought to a boil, charcoal added, and boiling continued for five minutes. Upon cooling, the suspension was filtered through Celite and the filtrate concentrated in vacuo to yield a solid, m.p. 226°-230°.

Workup

  1. temperatureThe reaction was refluxed for 22 hours
  2. concentrationconcentrated in vacuo to a solid which
  3. additionwas then added
  4. filtrationFiltration
  5. customprovided the free base as a semi-gum which
  6. additionadded
  7. temperatureUpon cooling
  8. filtrationthe suspension was filtered through Celite
  9. concentrationthe filtrate concentrated in vacuo
  10. customto yield a solid, m.p. 226°-230°

Sources & evidence

ORD record
ord-cb0c1604acbf44a68236af1dde3cf798
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Linked notes

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