Water → 3-Acetamido-2-chloro-4-(4-fluorophenylsulphanyl)aniline

HRID 2120356Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:6]([Cl:22])=[C:7]([N+:19]([O-])=O)[CH:8]=[CH:9][C:10]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:3])[CH3:2].O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Zn]>[C:1]([NH:4][C:5]1[C:6]([Cl:22])=[C:7]([CH:8]=[CH:9][C:10]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[NH2:19])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-acetamido-2-chloro-4-(4-fluorophenylsulphanyl)nitrobenzene (Method 15) (0.1 g), ferric chloride hexahydrate (0.238 g) and zinc dust (0.192 g in DMF (1 ml) and water (1 ml) was stirred and heated (oil bath 100° C.) for 1 hour then cooled. Water (15 ml) was added and the mixture was basified to pH 11 with saturated aqueous sodium carbonate solution (3 ml) then extracted with DCM (3×15 ml). The extracts were washed with brine then dried. Volatile material was removed by evaporation and the residue was left under high vacuum (2 mm Hg) overnight to give the title compound (0.087 g) as a solid. NMR: 1.95 (s, 3H), 5.72 (brs, 2H), 6.73 (d, 1H), 7.05-7.20 (m, 5H), 9.54 (brs, 1H); m/z: 309.

Workup

temperaturethen cooled
extractionthen extracted with DCM (3×15 ml)
washThe extracts were washed with brine
customthen dried
customVolatile material was removed by evaporation

Sources & evidence

ORD record: ord-5aee484bfc4d442e88f91e1940b46103
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689909B1

Reaction notes

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