Hydrochloric Acid → HCID 57901833, compound

HRID 1851629Notes

Reaction equation

HRID 1851629 reaction equation
[CH3:1][N:2]([S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8]2.[K].[OH-:24].[Na+].Cl.[O:27]1[CH2:31][CH2:30][CH2:29]C1>C(OCC)(=O)C.C(O)C.CN(C)C(=O)C.C(O)(=O)C>[CH3:1][N:2]([S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:14][C:30]([C:31]([OH:27])=[O:24])=[CH:29][N:13]=1)=[CH:8]2

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5462222PotassiumHCID 574759607-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

Product 1

HCID 57901833HCID 57901833, compoundYield 2.7%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (1.00 g), potassium (1-chloro-2-ethoxy-1-formyl-2-oxoethyl) (1.18 g), acetic acid (855 mg) and N,N-dimethylacetamide (20 mL) was stirred at 90° C. for 16 hr. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and filtrated. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography and eluted with an ethyl acetate-hexane (1:1) mixture to give a solid. The solid was mixed with tetrahydrofuran (3 mL), ethanol (3 mL) and 1N sodium hydroxide (5 mL), and the mixture was stirred at 60° C. for 3 days. The reaction mixture was acidified with 1N hydrochloric acid, diluted with ethyl acetate and washed with saturated brine. The organic layer was washed with sodium sulfate, filtrated, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with a methanol.ethyl acetate (1:5) mixture. The obtained solid was recrystallized from a methanol-ethyl acetate (1:10) mixed solvent to give the title compound (32 mg, yield 2.7%) as crystals. melting point 258-260° C.

Workup

  1. washwashed with saturated brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. washeluted with an ethyl acetate-hexane (1:1) mixture
  6. customto give a solid
  7. stirringthe mixture was stirred at 60° C. for 3 days
  8. washwashed with saturated brine
  9. washThe organic layer was washed with sodium sulfate
  10. filtrationfiltrated
  11. concentrationthe filtrate was concentrated
  12. washeluted with a methanol
  13. customThe obtained solid was recrystallized from a methanol-ethyl acetate (1:10)
  14. additionmixed solvent

Sources & evidence

ORD record
ord-ab5f1d05c03343c2afab9dabb5c2fd38
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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