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

HRID 504613Notes

Reaction equation

HRID 504613 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-0b7d80eebdfe4cf9881df0c0f20f000d
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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