Benzoyl chloride → N-(4-nitrostyrylsulfonyl)benzamide

HRID 839569Notes

Reaction equation

HRID 839569 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH:8]=[CH:9][S:10]([N:13]=[C:14](Cl)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+](C1C=CC(C=CS(N)(=O)=O)=CC=1)([O-])=[O:25].C(Cl)(=O)C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH:8]=[CH:9][S:10]([NH:13][C:14](=[O:25])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 24813Phosphorus oxychlorideHCID 536331802-(4-Nitrophenyl)ethene-1-sulfonamideHCID 54565141HCID 54565141, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Nitrostyrylsulfonyl)benzimidoyl chloride 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. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-5c93456cc3a54cb8ac1b188d532e897a
Source dataset
uspto-grants-1978_06
Patent number
US04096183

Reaction notes

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