Hydrochloric Acid → HCID 68285311, compound

HRID 1053252Notes

Reaction equation

HRID 1053252 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:9]([CH3:25])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17](=[O:24])(=[O:23])[N:18]=CN(C)C)=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Na+].O.Cl>C(O)C.C(OC(=O)C)C>[CH3:25][C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([S:17](=[O:24])(=[O:23])[NH2:18])=[CH:15][CH:16]=2)=[C:6]([C:4]([OH:5])=[O:3])[S:7][C:8]=1[N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68285843HCID 68285843, compound2×

Product 1

HCID 68285311HCID 68285311, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
97.5 °C

Procedure

Ethyl-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-4-methyl-5-morpholinothiophene-2-carboxylate (compound 24d, 0.36 g, 0.77 mmol) was suspended in ethanol (20 ml) and combined with 2N solution of NaOH (1.55 ml) at 25° C. The reaction mixture was heated at 95-100° C. under stirring for 1 hr. The progress of the reaction was monitored by TLC. The resulting reaction mixture was concentrated at a reduced pressure. The residue obtained was diluted with mixture of ethylacetate:water (30:15 ml). To this was added aqueous 10% HCl to bring the pH to between 5 and 6. The aqueous layer was extracted with ethyl acetate (2×20 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure from the dried organic layer to obtain the title compound (0.196 g, 66%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated at a reduced pressure
  3. customThe residue obtained
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×20 ml)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was evaporated under reduced pressure from the dried organic layer

Sources & evidence

ORD record
ord-387bf0e7d3f84697ac070d92cd31dbc5
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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