Ethyl Acetate → HCID 18473741, compound

HRID 2227448Notes

Reaction equation

HRID 2227448 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([NH:21][S:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27][CH:26]=4)(=[O:24])=[O:23])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].[C:34](OCC)(=O)[CH3:35]>S(Cl)(Cl)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([NH:21][S:22]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:30]=4)(=[O:24])=[O:23])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 18473749HCID 18473749, compound

Product 1

HCID 18473741HCID 18473741, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

N-{2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazol-5-yl}-(4-carboxy-benzenesulphonamide) (2.0 g, 4.3 mmol) is refluxed in 10 mL thionyl chloride for 1.5 h. The mixture is diluted with 50 mL ethyl acetate, the crystalline hydrochloride of the acid chloride is filtered off and washed with ethyl acetate/diethylether. The solid is suspended in 40 mL ethanol and slowly brought to reflux temperature. Half the ethanol is distilled off, the remainder is cooled and combined with ice water and made alkaline with aqueous potassium carbonate solution with stirring. It is diluted with water, the solid is filtered off and washed with water.

Workup

  1. filtrationthe crystalline hydrochloride of the acid chloride is filtered off
  2. washwashed with ethyl acetate/diethylether
  3. temperatureto reflux temperature
  4. distillationHalf the ethanol is distilled off
  5. temperaturethe remainder is cooled
  6. additionIt is diluted with water
  7. filtrationthe solid is filtered off
  8. washwashed with water

Sources & evidence

ORD record
ord-d4fe802941ac4bb3ad171437715dc1e7
Source dataset
uspto-grants-2002_07
Patent number
US06413990B1

Reaction notes

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