Methanesulfonyl chloride → HCID 46941444, compound

HRID 1812349Notes

Reaction equation

HRID 1812349 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N:9]([S:11]([CH3:10])(=[O:13])=[O:12])[S:11]([CH3:10])(=[O:13])=[O:12])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 46941444HCID 46941444, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-bromo-2-chloropyridin-3-amine (3.04 g, 14.7 mmol) of pyridine (20 mL) in 150-mL round-bottom flask, methanesulfonyl chloride (2.83 ml, 36.6 mmol) was added dropwise at 0° C. The ice bath was removed and the light brown solution was stirred at RT for overnight. Water (100 mL) was added and the precipitate was formed. The mixture was stirred at RT to break up lumps. The cream color solid was collcted via filtration and washed with water several times then air dried to afford N-(5-bromo-2-chloropyridin-3-yl)-N-(methylsulfonyl)methanesulfonamide (5.16 g, 96.9% yield) as a cream colored powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.65 (s, 6H), 8.69 (d, J=2.3 Hz, 1H), 8.75 (d, J=2.3 Hz, 1H). m/z (ESI, positive ion): 362.8 [M+H]+.

Workup

  1. customThe ice bath was removed
  2. additionWater (100 mL) was added
  3. customthe precipitate was formed
  4. stirringThe mixture was stirred at RT
  5. filtrationThe cream color solid was collcted via filtration
  6. washwashed with water several times
  7. customair dried

Sources & evidence

ORD record
ord-4776d9136ae24558932768093c725e4e
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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