Sulfuric Acid → 2-Chloro-5-bromo-[(beta-chloroethyl)-sulfonylmethylamino]-benzoic acid

HRID 1438843Notes

Reaction equation

HRID 1438843 reaction equation
S(=O)(=O)(O)O.O[CH2:7][S:8]([CH2:11][CH2:12][Cl:13])(=[O:10])=[O:9].[Cl:14][C:15]1[C:23]([NH2:24])=[CH:22][C:21]([Br:25])=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]>C(#N)C>[Cl:14][C:15]1[C:23]([NH:24][CH2:7][S:8]([CH2:11][CH2:12][Cl:13])(=[O:10])=[O:9])=[CH:22][C:21]([Br:25])=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 213993193-Amino-5-bromo-2-chlorobenzoic acidHCID 23462655Hydroxymethyl-(beta-chloroethyl)-sulfone

Product 1

HCID 213993372-Chloro-5-bromo-[(beta-chloroethyl)-sulfonylmethylamino]-benzoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

1 ml of concentrated sulfuric acid, followed by 9.6 g (60 mmoles) of hydroxymethyl-(β-chloroethyl)-sulfone were added at 60° C, whilst stirring, to a filtered solution of 12.6 g (50 moles) of 2-chloro-5-bromo-3-aminobenzoic acid in 150 ml of hot acetonitrile. The mixture was stirred for a further 2.5 hours at 50° C and was then cooled to 10° C, and the product which had precipitated was filtered off. It was rinsed with water and dried in air. 15 g (77% of theory) of 2-chloro-5-bromo-[(β-chloroethyl)-sulfonylmethylamino]-benzoic acid were obtained in the form of a yellow powder of melting point 164° C (with decomposition).

Workup

  1. additionwere added at 60° C
  2. temperaturewas then cooled to 10° C
  3. customthe product which had precipitated
  4. filtrationwas filtered off
  5. washIt was rinsed with water
  6. customdried in air

Sources & evidence

ORD record
ord-c32f3284cb514606bb40abb148d3030e
Source dataset
uspto-grants-1977_11
Patent number
US04057418

Reaction notes

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