Dimethyl Sulfoxide → 2-(1-Sulfonylamino-2-methylphenyl)ethylamine hydrochloride

HRID 1900103Notes

Reaction equation

C1(C)C=CC(C[CH2:8][NH2:9])=CC=1.F[C:12]1[CH:20]=[CH:19][C:18](F)=C[C:13]=1[C:14]([Cl:16])=O.C[NH:23][C:24](=O)[C:25](Cl)(Cl)Cl.[OH-:30].[Na+].C[S:33](C)=[O:34]>>[ClH:16].[S:33](=[N:23][C:24]1([CH2:25][CH2:8][NH2:9])[CH:18]=[CH:19][CH:20]=[CH:12][CH:13]1[CH3:14])(=[O:34])=[O:30]

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide

HCID 14798Sodium Hydroxide

HCID 76751p-Methylphenethylamine

HCID 2486522,2,2-Trichloro-n-methylacetamide

HCID 5880822,5-Difluorobenzoyl chloride

Product 1

HCID 865852052-(1-Sulfonylamino-2-methylphenyl)ethylamine hydrochloride

Procedure

2-(1-Sulfonylamino-2-methylphenyl)ethylamine hydrochloride, which is synthesized in accordance with Example 4 from 2-(p-tolyl)ethylamine, can be converted into 2,5-difluoro-N-{5-[1-sulfonylamino-N-(methylaminocarbonyl)-2methylphenyl]-ethyl}-benzamide, melting point: 196°-198° C., as described first with 2,5-difluorobenzoyl chloride and then with N-methyltrichloroacetamide and sodium hydroxide in dimethyl sulfoxide.

Sources & evidence

ORD record: ord-7e0140638caa456cbd151908c18e89d8
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574069

Reaction notes

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