Benzenesulfonyl chloride → HCID 10319531, compound

HRID 2396374Notes

Reaction equation

HRID 2396374 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:18]1([S:24]([NH:1][C:2]2[C:10]3[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=3[Cl:11])[NH:4][C:3]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 15043966HCID 15043966, compound

Product 1

HCID 10319531HCID 10319531, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Mix 3-amino-2-carbethoxy-4,6-dichloroindole (3.31 g, 12.1 mmol) and anhydrous pyridine (50 mL). Add, by dropwise addition, phenylsulfonyl chloride (2.35 g, 13.33 mmol). Stir for 48 hours at room temperature. Pourinto 1N hydrochloric acid (500 mL), extract with ethyl acetate and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize (ethyl acetate/hexane) to give the title compound (3.15 g, 63%); mp 245°-7° C.

Workup

  1. extractionPourinto 1N hydrochloric acid (500 mL), extract with ethyl acetate
  2. dry with materialdry (MgSO4)
  3. customEvaporate the solvent in vacuo
  4. customrecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-339370d81e1846e2b5ae444952059053
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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