Water → N-[4-(2,6-dibromo-pyridine-4-sulfonyl)-phenyl]-acetamide

HRID 1603560Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([Br:11])[N:3]=1.[Na+].[C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([S:23]([C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:13](=[O:15])[CH3:14])=[CH:22][CH:21]=2)(=[O:25])=[O:24])[CH:5]=[C:4]([Br:11])[N:3]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a solution of 63.7 g (0.226 Mol) 2,6-dibromo-4-nitropyridine in dimethylformamide (600 ml) at -15° C. were slowly added 50.0 g (0.226 Mol) 4-acetamido-benzenesulfinic acid sodium salt. The mixture was stirred at 15° C. for 3.5 h. Then 2.0 l water were added. It was stirred for another hour, filtered and the residue on the filter was washed with water (150 ml). It was then dissolved in aceton (hot, 700 ml) and evaporated. The residue was suspended in toluene (700 ml) and evaporated, again suspended in toluene and filtered. The residue on the filter was washed with toluene (200 ml) and dried in a high vacuum. It was obtained 67.3 g (69%) N-[4-(2,6-dibromo-pyridine-4-sulfonyl)-phenyl]-acetamide as a bright beige powder; mp.: 211° C.

Workup

customat -15° C.
stirringIt was stirred for another hour
filtrationfiltered
washthe residue on the filter was washed with water (150 ml)
dissolutionIt was then dissolved in aceton (hot, 700 ml)
customevaporated
customevaporated
filtrationfiltered
washThe residue on the filter was washed with toluene (200 ml)
customdried in a high vacuum

Sources & evidence

ORD record: ord-d8aa34c173a44a938a6f2ba1ebf5454a
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990105

Reaction notes

Loading…