Formic Acid → N-[Dichlorophosphinyl]-3-(4-nitrobenzenesulfonylamino)benzamide

HRID 27366Notes

Reaction equation

HRID 27366 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[P:23]([Cl:28])(Cl)(Cl)(Cl)[Cl:24].C(O)=[O:30]>C(Cl)(Cl)(Cl)Cl.[N+](C)([O-])=O>[Cl:24][P:23]([Cl:28])([NH:19][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH:15]=1)=[O:30]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 24819Phosphorus pentachlorideHCID 233427083-[[(4-Nitrophenyl)sulfonyl]amino]benzamide

Product 1

HCID 23342709N-[Dichlorophosphinyl]-3-(4-nitrobenzenesulfonylamino)benzamide

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6375NitromethaneSolvent

Procedure

A suspension of 32.1 g (0.1 m) of 3-[[(4-nitrophenyl)sulfonyl]-amino]-benzamide and 208 g (0.1 m) of phosphorous pentachloride in a mixture of 300 ml of carbon tetrachloride and 100 ml of nitromethane was stirred and heated for 90 min. The resulting solution was cooled to 20° and 4.7 g (0.1 m) of 97% formic acid added. The reaction was stirred overnight, then the product collected by filtration, washed with carbon tetrachloride and air-dried to give 36.7 g, melts 133°-134°, solidifies 138°, melts 188°-193°.

Workup

  1. temperatureheated for 90 min
  2. temperatureThe resulting solution was cooled to 20°
  3. stirringThe reaction was stirred overnight
  4. filtrationthe product collected by filtration
  5. washwashed with carbon tetrachloride
  6. customair-dried
  7. customto give 36.7 g
  8. custommelts 133°-134°
  9. customsolidifies 138°
  10. custommelts 188°-193°

Sources & evidence

ORD record
ord-4ffb1226bfa444dbad2a90e64514c952
Source dataset
uspto-grants-1980_09
Patent number
US04221730

Reaction notes

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