2-Mercaptoethanol → 3-Fluoro-4-[(2-hydroxyethyl)sulfanyl]benzene-1-sulfonamide

HRID 2118581Notes

Reaction equation

[H-].[Na+].[SH:3][CH2:4][CH2:5][OH:6].CN(C)C=[N:10][S:11]([C:14]1[CH:19]=[CH:18][C:17](F)=[C:16]([F:21])[CH:15]=1)(=[O:13])=[O:12]>CN(C=O)C>[OH:6][CH2:5][CH2:4][S:3][C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH2:10])(=[O:13])=[O:12])=[CH:15][C:16]=1[F:21]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (1.11 g, 50% oil dispersion, 0.023 mol) was washed with petroleum ether then suspended in freshly degassed DMF (50 ml). 2-Mercaptoethanol (1.8 g, 0.023 mol) was added dropwise under nitrogen. When gas evolution ceased, N,N-Dimethyl-N'-(3,4-difluorobenzenesulfonyl)formamidine (5 g, 0.02 mol) was added and the mixture was heated in an oil bath about 2 hours (80° C.). DMF was removed in vacuo and the residue was treated with 100 ml of 10% NaOH. After an additional hour of stirring the solution was acidified with concentrated HCl and extracted with ethylacetate (2×100 ml), and dried over anhydrous magnesium sulfate. Removal of solvent left 3 g of a white solid which when recrystallized from butyl chloride had m.p.=109°-111° C.

Workup

customDMF was removed in vacuo
additionthe residue was treated with 100 ml of 10% NaOH
extractionextracted with ethylacetate (2×100 ml)
dry with materialdried over anhydrous magnesium sulfate
customRemoval of solvent
waitleft 3 g of a white solid which when
customrecrystallized from butyl chloride

Sources & evidence

ORD record: ord-9eab6a954b13479c92f87fb5dcdd7c7a
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04678855

Reaction notes

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