Hydrochloric Acid → ethyl 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

HRID 1960239Notes

Reaction equation

HRID 1960239 reaction equation
COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl.C(O)C>O>[CH3:22][N:13]([S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:16])[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[NH:4][C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 57475950ethyl 1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 57475952ethyl 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (1.06 g), concentrated hydrochloric acid (1 ml) and ethanol (5 ml) was heated overnight under reflux. Water was added to the reaction mixture, and the resulting crystals were collected by filtration, washed with water, and dried. The obtained crystals were subjected to silica gel column chromatography to give the title compound (0.43 g, yield 46%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 164-165° C.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-67a5ab50488e41ac8c3c7ca844b1cd57
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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