4-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid → HCID 68136852, compound

HRID 1606620Notes

Reaction equation

HRID 1606620 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:14](Cl)(=O)=O)[C:12]=1[Cl:13])[C:7]([OH:9])=[O:8])([O-])=O>C(O)(=O)C.Cl>[ClH:13].[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([SH:14])[C:12]=1[Cl:13])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid

Product 1

HCID 68136852HCID 68136852, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-nitro-4-chloro-5-chlorosulfonylbenzoic acid (33 g.; 0.11 mole) in acetic acid (550 ml.) is warmed to 70° C. on a water bath and treated in one portion with a solution of stannous chloride dihydrate (226 g.; 1.0 mole) in concentrated hydrochloride acid (190 ml.). The reaction is stirred at 70°-80° C. for one-half hour, chilled in ice and the tin complex which separates is filtered, rinsed with acetic acid and dissolved in water (300 ml.). The solution is treated with concentrated hydrochloric acid (150 ml.) whereupon 3-amino-4-chloro-5-mercaptobenzoic acid hydrochloride separates, m.p. = 239.5° C.; yield, 20.5 g. (77%).

Workup

  1. temperaturechilled in ice
  2. filtrationthe tin complex which separates is filtered
  3. washrinsed with acetic acid
  4. dissolutiondissolved in water (300 ml.)
  5. additionThe solution is treated with concentrated hydrochloric acid (150 ml.) whereupon 3-amino-4-chloro-5-mercaptobenzoic acid hydrochloride
  6. customyield

Sources & evidence

ORD record
ord-12dacfd66de14c1c8b19d21fab2a3c9a
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

Loading…