p-Toluidine → Benzenesulfonamide, N-(4-methylphenyl)-4-nitro-

HRID 1186639Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].NC1C=CC(C)=CC=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:15]=[CH:20][C:17]([CH3:16])=[CH:18][CH:19]=2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 7813p-Toluidine

HCID 779038HCID 779038, compound

Product 1

HCID 293081Benzenesulfonamide, N-(4-methylphenyl)-4-nitro-Yield 97%

Procedure

(RK1-1-29)I This compound was prepared according to the procedure described for compound 11a except using p-toluidine to obtain required product as a yellow solid, (256 mg, 97%). Mp=170-172° C. (lit 184-184.5° C. Bioorganic and Medicinal Chemistry 15(2), 1014-1021; 2007); 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=9.0 Hz, 2H), 7.88 (d, J=9.0 Hz, 2H), 7.08 (d, J=8.2 Hz, 2H), 6.94 (d, J=8.2 Hz, 2H), 6.41 (bs, 1H), 2.30 (s, 3H).

Workup

custom(RK1-1-29)I This compound was prepared

Sources & evidence

ORD record: ord-961b2154f68e4004bcb79e72d70b85d1
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673910B2

Reaction notes

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