Sodium Carbonate → 6-chloro-N-(3-methylsulphonylaminobenzyl)nicotinamide

HRID 1246012Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][S:12]([NH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20])(=[O:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:32])=O>>[Cl:32][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([NH:15][S:12]([CH3:11])(=[O:14])=[O:13])[CH:17]=2)=[O:8])=[CH:4][N:3]=1

Participants

Reactant 4

HCID 10340Sodium Carbonate

HCID 24386Thionyl Chloride

HCID 2389326-Bromonicotinic acid

HCID 10495443N-[3-(Aminomethyl)phenyl]methanesulfonamide

Product 1

HCID 219145456-chloro-N-(3-methylsulphonylaminobenzyl)nicotinamide

Procedure

6-Bromonicotinic acid (200 mg, 0.99 mmol) was heated at reflux in thionyl chloride (2 ml) for 3 hrs. The reaction was allowed to cool to room temperature and the excess thionyl chloride evaporated under vacuum. The residue was dissolved in DCM (2 ml), 3-methylsulphonylaminobenzylamine (200 mg, 0.10 mmol) and sodium carbonate (500 mg) were added to the solution. The reaction was stirred at room temperature for 4 hrs, filtered and the filtrate reduced to dryness under vacuum to give 6-chloro-N-(3-methylsulphonylaminobenzyl)nicotinamide. NMR: δH [2H6]-DMSO 9.30,(1H, t), 8.88,(1H, d), 8.28,(1H, dd), 7.67,(1H, d), 7.23,(1H, t), 7.10,(1H, s), 7.04,91H, d), 6.97,(1H, d), 4.45,(2H, d), 2.90,(3H, s).

Workup

customthe excess thionyl chloride evaporated under vacuum
dissolutionThe residue was dissolved in DCM (2 ml)
filtrationfiltered

Sources & evidence

ORD record: ord-57914acc94d846b9a3f59b9d5a1c371a
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125898B2

Reaction notes

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