Hydrochloric Acid → 4'-(4-Chloro-2-phenylimidazol-1-ylmethyl)biphenyl-2-sulfonamide

HRID 1019250Notes

Reaction equation

HRID 1019250 reaction equation
CN(C=[N:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[C:26](C=O)=[C:25]([Cl:29])[N:24]=[C:23]3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:17][CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])C.Cl.C(O)C>O>[Cl:29][C:25]1[N:24]=[C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:22]([CH2:21][C:18]2[CH:17]=[CH:16][C:15]([C:10]3[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:20][CH:19]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 867577064'-(4-Chloro-5-formyl-2-phenylimidazol-1-ylmethyl)biphenyl-2-sulfonic acid dimethylaminomethylenamide

Product 1

HCID 184000964'-(4-Chloro-2-phenylimidazol-1-ylmethyl)biphenyl-2-sulfonamideYield 0.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.2 g of 4′-(4-chloro-5-formyl-2-phenylimidazol-1-ylmethyl)biphenyl-2-sulfonic acid dimethylaminomethylenamide (Example 11a), 95 ml of a saturated aqueous HCl solution and 95 ml of ethanol are refluxed for 2 h. After cooling, the mixture is diluted with 500 ml of water and extracted twice using 500 ml of EA each time and the organic phase is washed twice using 100 ml of a saturated aqueous NaCl solution each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. The product mixture is recrystallized from 200 ml of EA and 6.2 g of 4′-(4-chloro-5-formyl-2-phenyl-imidazol-1-ylmethyl)biphenyl-2-sulfonamide (compare Example 11b) are obtained. The solvent of the mother liquor is removed in vacuo and the residue is chromatographed on silica gel using MTB/DIP 1:1. 40 mg of a colorless oil are obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice
  3. washthe organic phase is washed twice
  4. dry with materialThe extract is dried over Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe product mixture is recrystallized from 200 ml of EA and 6.2 g of 4′-(4-chloro-5-formyl-2-phenyl-imidazol-1-ylmethyl)biphenyl-2-sulfonamide (compare Example 11b)
  7. customare obtained
  8. customThe solvent of the mother liquor is removed in vacuo
  9. customthe residue is chromatographed on silica gel using MTB/DIP 1:1

Sources & evidence

ORD record
ord-6f2b90c4a9824f5d9b8b0abaa4cd68ea
Source dataset
uspto-grants-2002_11
Patent number
US06486189B2

Reaction notes

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