Hydrochloric Acid → Ethyl 5-chloro-3-phenylsulfonylindole-2-carboximidate

HRID 260495Notes

Reaction equation

HRID 260495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:12])=[C:5]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].Cl.[CH2:23]([OH:25])[CH3:24]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[NH:12])[O:25][CH2:23][CH3:24])=[C:5]2[S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 224015145-chloro-3-(phenylsulfonyl)-1H-Indole-2-carbonitrile

Product 1

HCID 135761968Ethyl 5-chloro-3-phenylsulfonylindole-2-carboximidate

Procedure

5-Chloro-3-phenylsulfonylindole-2-carbonitrile is allowed to react with ethanol saturated with hydrogen chloride at 0°-10° C. for 7 days. Evaporation to dryness affords the title compound as a hydrochloride salt. The title compound is obtained as a free base by adding the reaction mixture to an ice cold solution of excess potassium carbonate and extracting the product with chloroform.

Workup

  1. customEvaporation to dryness

Sources & evidence

ORD record
ord-b5ca2beacb904c069c533ceac9550f73
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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