Hydrochloric Acid → HCID 68278778, compound

HRID 1506899Notes

Reaction equation

HRID 1506899 reaction equation
[C:1]1([S:7]([N:10](S(C2C=CC=CC=2)(=O)=O)[C:11]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].Cl>O1CCOCC1.O>[C:1]1([S:7]([NH:10][C:11]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86693763HCID 86693763, compound2×

Product 1

HCID 68278778HCID 68278778, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-[bis-(benzenesulphonyl)amino]benzo[b]thiophene-3-carboxylate (Intermediate 4, 0.173 g) and lithium hydroxide mono hydrate (0.043 g) in dioxane (6 ml) and water (3 ml) was stirred and heated at 60° C. for 2.5 hours. After cooling, the mixture was diluted with water and acidified by addition of hydrochloric acid (1M). It was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane (5-10%) to give ethyl 2-benzenesulphonylaminobenzo[b]thiophene-3-carboxylate (0.075 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionIt was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and pentane (5-10%)

Sources & evidence

ORD record
ord-08e628acd9914523aa28153208125395
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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