Sulfuric Acid → HCID 54345768, compound

HRID 1438844Notes

Reaction equation

HRID 1438844 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:8][C:9](=[O:19])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([NH2:17])[C:11]=1[Cl:18])[CH3:7].O[CH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>O>[CH2:6]([O:8][C:9](=[O:19])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([NH:17][CH2:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:11]=1[Cl:18])[CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 18994119Ethyl 3-amino-2,5-dichlorobenzoateHCID 19820153HCID 19820153, compound

Product 1

HCID 54345768HCID 54345768, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of concentrated sulfuric acid was added to 2.32 g (10mmoles) of 2,5-dichloro-3-aminobenzoic acid ethyl ester, 2.27 g (11mmoles) of hydroxymethyl-(4-chlorophenyl)-sulfone and 40 ml of water whilst stirring at room temperature. The mixture was stirred for a further 3 hours at room temperature, the solid was filtered off and dissolved in about 100 ml of methylene chloride, the solution was dried over magnesium sulfate and worked up in the usual manner and the product was recrystallized from ethylene chloride. 3.0 g (71% of theory) of 2,5-dichloro-3-[(4-chlorophenyl)-sulfonylmethylamino]-benzoic acid ethyl ester were obtained in the form of colorless crystals of melting point 173°-175° C.

Workup

  1. stirringThe mixture was stirred for a further 3 hours at room temperature
  2. filtrationthe solid was filtered off
  3. dissolutiondissolved in about 100 ml of methylene chloride
  4. dry with materialthe solution was dried over magnesium sulfate
  5. customthe product was recrystallized from ethylene chloride

Sources & evidence

ORD record
ord-940a81a65d644590b07f98b76862b519
Source dataset
uspto-grants-1977_11
Patent number
US04057418

Reaction notes

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