Sulfuric Acid → 2,5-Dichloro-3-[(beta-chloroethyl)-sulfonylmethylamino]-benzoic acid

HRID 1438842Notes

Reaction equation

[Cl:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O[CH2:14][S:15]([CH2:18][CH2:19][Cl:20])(=[O:17])=[O:16].S(=O)(=O)(O)O>C(Cl)CCl>[Cl:1][C:2]1[C:10]([NH:11][CH2:14][S:15]([CH2:18][CH2:19][Cl:20])(=[O:17])=[O:16])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 40 °C

Procedure

20.6 g (0.1 mole) of 2,5-dichloro-3-aminobenzoic acid and 18.7 g (0.12 mole) of hydroxymethyl-(β-chloroethyl)-sulfone were suspended in 100 ml of ethylene chloride, 1 ml of concentrated sulfuric acid was added thereto and the mixture was stirred for 3 hours at 40° C. The mixture was then cooled and the product which had crystallized out was filtered off and recrystallized from acetonitrile. This gave 30.8 g (89% of theory) of 2,5-dichloro-3-[(β-chloroethyl)-sulfonylmethylamino]-benzoic acid in the form of colorless crystals of melting point 156° C (with decomposition).

Workup

temperatureThe mixture was then cooled
customthe product which had crystallized out
filtrationwas filtered off
customrecrystallized from acetonitrile

Sources & evidence

ORD record: ord-5d508dae9bf74e0995ef3ae157cc604e
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04057418

Reaction notes

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