Hydrochloric Acid → HCID 68285893, compound

HRID 1053302Notes

Reaction equation

HRID 1053302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[C:20]([CH3:28])[CH:19]=3)[C:9]=2[CH3:29])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[C:20]([CH3:28])[CH:19]=3)[C:9]=2[CH3:29])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68285619HCID 68285619, compound

Product 1

HCID 68285893HCID 68285893, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

Ethyl 5-(4-chlorophenyl)-4-methyl-3-(3-methyl-4-sulfamoylphenyl)thiophene-2-carboxylate (41c, 0.6 g, 1.33 mmol) was suspended in ethanol (20 ml) and a solution of sodiumhydroxide (0.1 g, 2.66 mmol) in water (2 ml] was added to it at 25° C. The reaction mixture was then heated at 75° C. under stirring for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue so obtained was then diluted with water (5 ml) and the mixture was cooled using ice bath. To the cooled mixture was added 10% aqueous HCl to bring the pH of the mixture between about 5 and 6. The mixture was then extracted with ethyl acetate (2×35 ml). The combined organic layer was then dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain the title compound (0.53 g, 94%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturethe mixture was cooled
  4. extractionThe mixture was then extracted with ethyl acetate (2×35 ml)
  5. dry with materialThe combined organic layer was then dried over anhydrous Na2SO4
  6. customThe solvent was evaporated from the dried organic layer under reduced pressure

Sources & evidence

ORD record
ord-acfb0b6444bc4c30b5ccb29cc7e537e6
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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