Benzoyl chloride → N-(4-nitrostyrylsulfonyl)benzamide

HRID 1706093Notes

Reaction equation

HRID 1706093 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 1.5 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 1.5 hr
  2. additionThe reaction mixture diluted with 20 ml
  3. filtrationfiltered
  4. customaffords 19.0 g

Sources & evidence

ORD record
ord-04c97fc20a7f4bc8a3c2f9d9073e4ff2
Source dataset
uspto-grants-1980_06
Patent number
US04206142

Reaction notes

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