Indole → HCID 67316169, compound

HRID 750623Notes

Reaction equation

HRID 750623 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[S:13](=[O:21])(=[O:20])[N:12]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[S:13](=[O:20])(=[O:21])[N:12]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 64783Pseudosaccharin chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67316169HCID 67316169, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

Indole (117 mg, 1 mmol) and 3-chloro-benzo[d]isothiazole 1,1-dioxide (201 mg, 1 mmol) were treated 5 mL of 1,2-dichloroethane followed by AlCl3 (160 mg, 1.2 mmol). The reaction mixture was heated to 65° C. overnight, then cooled and quenched with water (1 mL). The resulting solid was filtered, washed with water, and dried to give 0.3 grams of the sub-title compound. MS: ESI (negative): 281 (M−H).

Workup

  1. temperaturecooled
  2. customquenched with water (1 mL)
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-564e41620e744d36b143a17dc547f292
Source dataset
uspto-grants-2008_07
Patent number
US07405215B2

Reaction notes

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