Benzoyl chloride → N-(4-nitrostyrylsulfonyl)benzamide

HRID 128425Notes

Reaction equation

HRID 128425 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-224cf17aaa994887ad91e1521c6b14af
Source dataset
uspto-grants-1981_03
Patent number
US04259482

Reaction notes

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