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

HRID 2233614Notes

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-methylsulphonylarninobenzylamine (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-827ca0a3a2e2460d923af4c13b60da33
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709506B2

Reaction notes

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