Cyclopropylamine → 4,5-Dichloro-2-cyclopropylaminobenzenesulphonamide

HRID 17835

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:4](F)[CH:3]=1.[CH:14]1([NH2:17])[CH2:16][CH2:15]1>O1CCOCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:4]([NH:17][CH:14]2[CH2:16][CH2:15]2)[CH:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of 4,5-dichloro-2-fluorobenzenesulphonamide (3 g) in dioxane (30 mL) to which cyclopropylamine (3 mL) has been added is heated at 100-110° C. in a hermetically closed vessel for 24 hours. The solvent and the excess of amine are removed by distillation under reduced pressure and the residue is dissolved in methanol (20 mL). The methanolic solution is cooled on an ice bath, and water (60 mL) is added. The precipitate obtained (the title product) is collected by filtration, washed with water and dried. It is used in the following Step without being otherwise purified.

Workup

customThe solvent and the excess of amine are removed by distillation under reduced pressure
dissolutionthe residue is dissolved in methanol (20 mL)
temperatureThe methanolic solution is cooled on an ice bath
additionwater (60 mL) is added

Sources & evidence

ORD record: ord-8df3b2af4ad44a3c9cd5221054a83a8f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741320B2

Linked notes

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