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

HRID 2037239Notes

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-f7e8764d2e5f437ca5d5acf546fcd67f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575204B2

Reaction notes

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