Acetic Anhydride → HCID 21544097, compound

HRID 1606625Notes

Reaction equation

HRID 1606625 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:6]=[C:7]([I:9])[CH:8]=1)#[N:2].[H-].[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C)C=O>[C:16]([NH:13][S:10]([C:5]1[CH:6]=[C:7]([I:9])[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)(=[O:12])=[O:11])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 21544101HCID 21544101, compound

Product 1

HCID 21544097HCID 21544097, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.08 g. (10 mmoles) of 3-cyano-5-iodobenzenesulfonamide in 30 ml. of dimethylformamide is treated with 420 mg. (10 mmoles) of 57% sodium hydride emulsion. When the initial reaction subsides, the mixture is heated in a warm water bath for one hour. 2.8 Ml. (30 mmoles) of acetic anhydride is added and the solution becomes cloudy. The mixture is stirred for one hour and poured into an ice water mixture. After 30 minutes of stirring, the precipitate is filtered, washed with water, methanol and ether affording 2.97 g. (85%) of N-acetyl-3-cyano-5-iodobenzenesulfonamide melting point 249° to 251°C.

Workup

  1. customWhen the initial reaction subsides
  2. temperaturethe mixture is heated in a warm water bath for one hour
  3. stirringAfter 30 minutes of stirring
  4. filtrationthe precipitate is filtered
  5. washwashed with water, methanol and ether affording 2.97 g

Sources & evidence

ORD record
ord-87df43ab9d2f4de7b6c6ca943291008d
Source dataset
uspto-grants-1976_04
Patent number
US03953492

Reaction notes

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