Phosphorus oxychloride → 4-Amino-3-nitrobenzene-1-sulfonyl chloride

HRID 29153Notes

Reaction equation

HRID 29153 reaction equation
[Na+].[N+:2]([C:5]1[CH:11]=[C:10]([S:12]([O-:15])(=O)=[O:13])[CH:9]=[CH:8][C:6]=1[NH2:7])([O-:4])=[O:3].P(Cl)(Cl)([Cl:18])=O>>[N+:2]([C:5]1[CH:11]=[C:10]([S:12]([Cl:18])(=[O:15])=[O:13])[CH:9]=[CH:8][C:6]=1[NH2:7])([O-:4])=[O:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 165281Sodium 4-amino-3-nitrobenzenesulfonate

Product 1

HCID 129630684-Amino-3-nitrobenzene-1-sulfonyl chlorideYield 87.1%

Procedure

A mixure of o-nitroaniline-p-sulfonic acid sodium salt (25.00 g, 104 mmol) and phosphoryl chloride (75 mL, 804 mmol) under Argon was heated to reflux and vigorously stirred for 4 hours. After cooling to ambient temperature, the reaction mixture was carefully added to a large excess of ice. The resulting slurry was stirred for 15 min., filtered and dried under vacuum to provide o-nitroaniline-p-sulfonyl chloride (21.43 g, 87%) as a yellow solid. H1-NMR (dimethylsulfoxide-D6): 5.8 (b, 2H), 6.97 (d, 1H, J=8.8), 7.57 (m, 1H), 8.18 (d, 1H, J=2.0).

Workup

  1. temperatureto reflux
  2. additionthe reaction mixture was carefully added to a large excess of ice
  3. stirringThe resulting slurry was stirred for 15 min.
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-db43682ef7be4ef3862bcb735015bfe4
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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