Hydrochloric Acid → HCID 68286089, compound

HRID 1053278Notes

Reaction equation

HRID 1053278 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])=[CH:20][CH:19]=3)[C:9]=2[N:28]([CH3:30])[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:26])(=[O:27])[NH2:25])=[CH:20][CH:19]=3)[C:9]=2[N:28]([CH3:30])[CH3:29])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68285705HCID 68285705, compound2×

Product 1

HCID 68286089HCID 68286089, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

Ethyl 5-(4-chlorophenyl)-4-(dimethylamino)-3-(4-sulfamoylphenyl)thiophene-2-carboxylate (compound 34e, 2.00 g, 4.30 mmol) was suspended in ethanol (30 ml) and solution of NaOH (0.86 g, 21.5 mmol) in water (4 ml) was added to it at 25° C. The reaction mixture was then heated at 75° C. under stirring for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was diluted with water (10 ml) and cooled using ice bath. To the cooled mixture was added aqueous 10% HCl to bring the pH od the solution to about 6. The mixture so obtained was extracted with ethyl acetate (3×30 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 (1.60 g, 85.1%)

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturecooled
  4. customThe mixture so obtained
  5. extractionwas extracted with ethyl acetate (3×30 ml)
  6. dry with materialThe combined organic layer was then dried over anhydrous Na2SO4
  7. customThe solvent was evaporated from the dried organic layer under reduced pressure

Sources & evidence

ORD record
ord-98a3ac21abdf41438ef40814dff65a1b
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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