Benzoyl chloride → N-(4-nitrostyrylsulfonyl)benzamide

HRID 66208Notes

Reaction equation

HRID 66208 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. additionThe reaction mixture diluted with 20 ml
  3. filtrationfiltered
  4. customaffords 19.0 g

Sources & evidence

ORD record
ord-e331235367b8419f903d6f7379c922d5
Source dataset
uspto-grants-1978_12
Patent number
US04130663

Reaction notes

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