Hydrochloric Acid → HCID 178504596, compound

HRID 452778

Reaction equation

HRID 452778 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]([O:21]C)=O)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3].O.[NH2:24][NH2:25].[C:26](=[S:28])=S.C(N(CC)CC)C.Cl>CO.C(O)C.O>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:21][C:26]([SH:28])=[N:25][N:24]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 44482291Methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate

Product 1

HCID 178504596HCID 178504596, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate (2.23 g, 7.10 mmol) and hydrazine monohydrate (1.76 mL, 36.3 mmol) in methanol (25 mL) was heated under reflux for 4 days. After cooling, the reaction mixture was concentrated under reduced pressure, and a solution of the obtained residue, carbon disulfide (1.28 mL, 21.3 mmol) and triethylamine (1.19 mL, 8.52 mmol) in ethanol (30 mL) was heated under reflux for 4 hr. After cooling, the reaction mixture was poured into water, and the mixture was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran to give the title compound (1.19 g, yield 47%) as pale-yellow crystals.

Workup

  1. temperatureunder reflux for 4 days
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. temperatureunder reflux for 4 hr
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-ebd723acf2724f15b0c884783029fd0e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Linked notes

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