Water → 1H-indole-3-sulfonamide

HRID 1947053Notes

Reaction equation

HRID 1947053 reaction equation
C([NH:8][S:9]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=[O:11])=[O:10])(OC(C)(C)C)=O.[Na+].[I-].C[Si](Cl)(C)C.O>CC#N>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([S:9]([NH2:8])(=[O:11])=[O:10])=[CH:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 86620846HCID 86620846, compound

Product 1

HCID 189604091H-indole-3-sulfonamideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

N-Boc 1H-indole-3-sulfonamide (1.47 g, 4.96 mmol) was dissolved in CH3CN (75 mL), and NaI (3.72 g, 24.80 mmol) added. The mixture was cooled to 0° C. under N2, and tri-methylsilyl chloride (TMS-Cl, 2.69 g, 24.80 mmol) added dropwise, the mixture stirred for 15 min at 0° C., then stirred at RT overnight. The mixture was poured into water, the resulting off-white precipitate filtered, washed with water and hexane, and air dried to provide 1H-indole-3-sulfonic acid amide (947 mg, 97% yield), which was used without further purification.

Workup

  1. stirringstirred at RT overnight
  2. filtrationthe resulting off-white precipitate filtered
  3. washwashed with water and hexane, and air
  4. customdried

Sources & evidence

ORD record
ord-ba151e8301594a819c79f88d8472d82b
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

Loading…