Sodium Bicarbonate → N-{4-[4-(4-Nitro-1-oxidopyrid-3-yl)piperazin-1-yl]phenyl}methanesulphonamide

HRID 2232406Notes

Reaction equation

Cl.[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.NC1C=CN=C(N2CCN(C3C=CC(NS(C)(=O)=O)=CC=3)CC2)C=1.Cl[C:44]1[CH:45]=[N+:46]([O-:53])[CH:47]=[CH:48][C:49]=1[N+:50]([O-:52])=[O:51].C(=O)(O)[O-].[Na+]>C(O)CCC>[N+:50]([C:49]1[CH:48]=[CH:47][N+:46]([O-:53])=[CH:45][C:44]=1[N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:3][CH2:4]1)([O-:52])=[O:51]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-[(4-piperazin-1-yl)phenyl]methanesulphonamide hydrochloride (the product of Example 11, (iii) (0.59 g), 3-chloro-4-nitropyridine-N-oxide (0.35 g) and sodium bicarbonate (0.50 g) in n-butanol (25 ml) was heated at 100° C. with stirring for 1.5 hours and then evaporated. The residue was stirred with water, filtered, and the solid was crystallised from methanol to give the title compound (0.55 g), m.p. 206°-208° C. Found: C,48.77; H,4.91; N,17.52. C16H19N5O5S requires: C,48.84; H,4.87; N,17.80%.

Workup

customevaporated
stirringThe residue was stirred with water
filtrationfiltered
customthe solid was crystallised from methanol

Sources & evidence

ORD record: ord-83eaa1477f2840809921b8537ca37f28
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788196

Reaction notes

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