Hydrochloric Acid → 2-Benzenesulphonylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

HRID 1506891Notes

Reaction equation

HRID 1506891 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[S:15][C:14]3[CH2:16][CH2:17][CH2:18][CH2:19][C:13]=3[C:12]=2[C:20]([O:22]CC)=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1.O>[C:1]1([S:7]([NH:10][C:11]2[S:15][C:14]3[CH2:16][CH2:17][CH2:18][CH2:19][C:13]=3[C:12]=2[C:20]([OH:22])=[O:21])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 391240Ethyl 2-(benzenesulfonamido)-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate2×

Product 1

HCID 8726872-Benzenesulphonylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acidYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of potassium trimethylsilanoate (0.141 g) in dry THF (5 ml) was added to a cooled solution of ethyl 2-benzenesulphonylamino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylate (Intermediate 1, 0.076 g) in dry THF (5 ml). The resultant cloudy solution was stirred at room temperature for 2 hours. Further potassium trimethylsilanoate (0.076 g) was added and the resultant mixture was stirred for a total of 72 hours. The mixture was then stirred and heated at 60° C. for a total of 48 hours. The resultant mixture was diluted with water and acidified to pH1 by addition of concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether. The solid was collected by filtration and air dried to give 2-benzenesulphonylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (0.034 g) as an off white solid.

Workup

  1. stirringThe mixture was then stirred
  2. temperatureheated at 60° C. for a total of 48 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was triturated with ether
  9. filtrationThe solid was collected by filtration and air
  10. customdried

Sources & evidence

ORD record
ord-ab534f305a094005bf85473eab003621
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

Loading…