Sulfuric Acid → HCID 54165052, compound

HRID 1438845Notes

Reaction equation

HRID 1438845 reaction equation
S(=O)(=O)(O)O.[CH3:6][NH:7][C:8](=[O:18])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([NH2:16])[C:10]=1[Cl:17].O[CH2:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>O>[CH3:6][NH:7][C:8](=[O:18])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([NH:16][CH2:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:10]=1[Cl:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 19820153HCID 19820153, compoundHCID 54122859Benzamide, 3-amino-2,5-dichloro-N-methyl-

Product 1

HCID 54165052HCID 54165052, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.8 g of concentrated sulfuric acid was added to 1.8 g (8.2 mmoles) of 2,5-dichloro-3-aminobenzoic acid N-methylamide, 1.87 g (9 mmoles) of hydroxymethyl-(4-chlorophenyl)-sulfone and 50 ml of water whilst stirring at room temperature. The mixture was stirred for a further 2 hours at room temperature and the solid was then filtered off, washed with water and recrystallized from acetonitrile. 2.8 g (83% of theory) of 2,5-dichloro-3-[(4-chlorophenyl)-sulfonylmethylamino]-benzoic acid N-methylamide were obtained in the form of a colorless solid of melting point 175°-182° C (with decomposition).

Workup

  1. stirringThe mixture was stirred for a further 2 hours at room temperature
  2. filtrationthe solid was then filtered off
  3. washwashed with water
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-44c40bbe11444d4e856e4a851c53b7bd
Source dataset
uspto-grants-1977_11
Patent number
US04057418

Reaction notes

Loading…