Hydrochloric Acid → 4-amino-N-methyl-N-phenylbenzenesulfonamide

HRID 1938173Notes

Reaction equation

Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]P(Cl)(Cl)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:16][NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[OH-].[NH4+]>O>[C:18]1([N:17]([CH3:16])[S:2]([C:5]2[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of N-(4-chlorosulfonylphenyl)phosphoramidic dichloride (1.0 g) and N-methylaniline (2.49 g) in water (5 ml) was heated at reflux for 18 hours. After cooling to 0° C. and adjustment to pH2 with concentrated hydrochloric acid, the suspension was heated at reflux for 30 minutes, then cooled to 0° C. and adjusted to pH 8 with concentrated ammonium hydroxide. The suspension was extracted with ethyl acetate (3×40 ml), the combined organic extracts were washed with brine, dried (Na2SO4), and concentrated to an oil. Purification by chromatography (3:2 hexane: ethyl acetate) gave 4-(N-phenyl-N-methylaminosulfonyl)aniline as a colourless crystalline solid (0.65 g); MS: m/z=263(M+1); NMR (CDCl3): 3.13 (s,3), 4.11 (broad s,2), 6.58-6.62 (m, 2), 7.10-7.13 (m,2), 7.23-7.31 (m,s).

Workup

temperaturewas heated
temperatureat reflux for 18 hours
temperatureat reflux for 30 minutes
temperaturecooled to 0° C.
extractionThe suspension was extracted with ethyl acetate (3×40 ml)
washthe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated to an oil
customPurification by chromatography (3:2 hexane: ethyl acetate)

Sources & evidence

ORD record: ord-b4a7f5a949c9480a9fcadc2863244a75
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693639

Reaction notes

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