Ammonium Chloride → 3-Benzenesulfonyl-5-chloroindole-2-carboxamide

HRID 260479Notes

Reaction equation

HRID 260479 reaction equation
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=3)[NH:12][C:11]=2[C:20]([O:22]CC)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+:26]>[OH-].[NH4+]>[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=3)[NH:12][C:11]=2[C:20]([NH2:26])=[O:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 22401503Ethyl 3-phenylsulfonyl-5-chloroindole-2-carboxylate

Product 1

HCID 4548443-Benzenesulfonyl-5-chloroindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl 3-phenylsulfonyl-5-chloroindole-2-carboxylate (596 mg, 1.64 mmol) in aqueous conc. ammonium hydroxide (10 mL) containing ammonium chloride (28 mg) was heated at 100° C. for 3 hours in a sealed screw-top tube. The sealed tube was cooled in an ice bath as product crystallized out. The product was collected by filtration, rinsed with ice water, and dried to give the product, mp 253°-254° C.

Workup

  1. temperatureThe sealed tube was cooled in an ice bath as product
  2. customcrystallized out
  3. filtrationThe product was collected by filtration
  4. washrinsed with ice water
  5. customdried
  6. customto give the product, mp 253°-254° C.

Sources & evidence

ORD record
ord-1938ad879d994b299f62cfe8700855bb
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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