Acetic Anhydride → HCID 71772326, compound

HRID 1841828Notes

Reaction equation

HRID 1841828 reaction equation
S(=O)(O)[O-].[Na+:5].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[S:15]([O-:18])(=[O:17])=[O:16].[Na+].[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[C:20]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[S:15]([O-:18])(=[O:16])=[O:17])(=[O:22])[CH3:21].[Na+:5]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 23665763Sodium BisulfiteHCID 71772328HCID 71772328, compound

Product 1

HCID 71772326HCID 71772326, compoundYield 93%

Conditions

Temperature
70 °C

Procedure

To a round-bottom-flask containing 60 mL acetic anhydride was added 5 g sodium bisulfite and 5 g sodium indole-2-sulfonate. The mixture was heated and stirred at 70° C. for 1 hr and then at 90° C. for 2 hrs. Upon cooling, the solid was filtered, washed with ether, and dried to yield 5.7 g of sodium 1-acetylindole-2-sulfonate product (93%) as a white solid. The sodium 1-acetylindole-2-sulfonate product was used in the next step without further purification. MP>320° C.; IR (KBr, cm−1) 3480, 3010, 1660, 1490, 1400, 1385, 1150, 1050, 980, 760.

Workup

  1. temperatureThe mixture was heated
  2. waitat 90° C. for 2 hrs
  3. temperatureUpon cooling
  4. filtrationthe solid was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-dccb3fd262534e74a93075e8371d8868
Source dataset
uspto-grants-2015_02
Patent number
US08945397B2

Reaction notes

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