Hydrochloric Acid → HCID 57293271, compound

HRID 2082539Notes

Reaction equation

HRID 2082539 reaction equation
[C:1]1([S:7]([CH2:10][NH:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:22])=[CH:18][C:19]=3[Cl:21])[NH:14][C:13]=2[C:23]([O:25]CC)=[O:24])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.O.[OH-].[Li+].Cl>O>[C:1]1([S:7]([CH2:10][NH:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:22])=[CH:18][C:19]=3[Cl:21])[NH:14][C:13]=2[C:23]([OH:25])=[O:24])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57265194HCID 57265194, compound

Product 1

HCID 57293271HCID 57293271, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mix 3-[(phenylsulfonyl)methylamino]-2-carbethoxy-4,6-dichloroindole (185 mg, 0.433 mmol), tetrahydrofuran (25 mL) and water (25 mL). Add lithium hydroxide monohydrate (2.6 mmol) and stir at room temperature for 3 days, then at reflux for 5 hours. Pour into 1N hydrochloric acid (200 mL) and extract into ethyl acetate. Dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound (122 mg, 71%); mp 286°-90° C.

Workup

  1. temperatureat reflux for 5 hours
  2. extractionextract into ethyl acetate
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e66901c779bd44cd921013d0efd515d9
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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