Hydrochloric Acid → HCID 10430152, compound

HRID 2082537Notes

Reaction equation

HRID 2082537 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=3[Cl:20])[NH:13][C:12]=2[C:22]([O:24]CC)=[O:23])(=[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]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=3[Cl:20])[NH:13][C:12]=2[C:22]([OH:24])=[O:23])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 10319531HCID 10319531, compound

Product 1

HCID 10430152HCID 10430152, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

Mix 3-[(phenylsulfonyl)amino]-2-carbethoxy-4,6-dichloroindole (0.35 g, 0.847 mmol), tetrahydrofuran (10 mL) and water (7 mL). Add lithium hydroxide monohydrate (0.11 g, 2.54 mmol) and stir at room temperature overnight. Warm at 65° C. for 5 hours, pour into water and acidify to pH 1 with 1N hydrochloric acid. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound (0.2 g, 61%); mp 229°-35° C. (dec).

Workup

  1. extractionExtract into ethyl acetate
  2. dry with materialdry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f81aa352d4b4d0ab0e8bfeb33cd6a15
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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