Ethylene Glycol → HCID 57901635, compound

HRID 1851521Notes

Reaction equation

HRID 1851521 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19](=[S:21])[NH2:20])=[CH:15]2)(=[O:8])=[O:7].N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1S.Cl.C(O)CO>O>[S:21]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:20]=[C:19]1[C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:7])=[O:8]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 87132-AminothiophenolHCID 57901763HCID 57901763, compound

Product 1

HCID 57901635HCID 57901635, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.30 g), 2-aminothiophenol (0.10 mL), concentrated hydrochloric acid (0.5 mL) and ethylene glycol (6 mL) was stirred at 100° C. overnight. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (0.14 g, yield 38%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 201-202° C.

Workup

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-8c958880148d444dbdd06db112f76a8b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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