Benzoyl chloride → N-(4-nitrostyrylsulfonyl)benzamide

HRID 972300Notes

Reaction equation

HRID 972300 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[CH:9][S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][S:10]([NH:13][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:11])=[O:12])=[CH:14][CH:15]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24813Phosphorus oxychlorideHCID 536331802-(4-Nitrophenyl)ethene-1-sulfonamide

Product 1

HCID 54406439N-(4-nitrostyrylsulfonyl)benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitrostyrylsulfonamide (18.2 g., 0.08 mole), benzoyl chloride (12.6 g., 0.09 mole) and phosphorus oxychloride (13.8 g., 0.09 mole) is heated at steam bath temperature for 105 hr. The reaction mixture diluted with 20 ml. of ethyl acetate, cooled and filtered affords 19.0 g. (76% yield) of N-(4-nitrostyrylsulfonyl)benzamide, m.p. 192°-195° C., from ethyl acetate-hexane.

Workup

  1. temperatureis heated at steam bath temperature for 105 hr
  2. additionThe reaction mixture diluted with 20 ml
  3. filtrationfiltered
  4. customaffords 19.0 g

Sources & evidence

ORD record
ord-31e1cb9f2454463bb4c05d683ba4c096
Source dataset
uspto-grants-1977_10
Patent number
US04052455

Reaction notes

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