Methanesulfonyl chloride → N-(4-cyanopyridin-2-yl)-methanesulfonamide

HRID 219669Notes

Reaction equation

HRID 219669 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[C:5]([C:4]1[CH:7]=[CH:8][N:9]=[C:2]([NH:1][S:11]([CH3:10])(=[O:13])=[O:12])[CH:3]=1)#[N:6]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 70155242-Aminoisonicotinonitrile

Product 1

HCID 69122739N-(4-cyanopyridin-2-yl)-methanesulfonamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-isonicotinonitrile (1 g, 8.4 mmol) and methanesulfonyl chloride (0.716 mL, 9.2 mmol) in pyridine (10 mL) is stirred at room temperature for 12 hours. The mixture is poured onto ice and stirred for 20 min. The mixture is filtered and washed with water (100 mL), followed by diethyl ether (100 mL). The solid is dried in vacuo to afford N-(4-cyanopyridin-2-yl)-methanesulfonamide (1.1 g, 66%). MS: 198 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 3.32 (s, 3H), 7.27 (s, 1H), 7.48 (d, J=5.1 Hz, 1H), 8.53 (d, J=5.3 Hz, 1H).

Workup

  1. additionThe mixture is poured onto ice
  2. filtrationThe mixture is filtered
  3. washwashed with water (100 mL)
  4. customThe solid is dried in vacuo

Sources & evidence

ORD record
ord-a936359a7f7140339e0b82fb11638319
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…