Pyridine → HCID 86628176, compound

HRID 1158654Notes

Reaction equation

HRID 1158654 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][N:14]([CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[S:15]([CH3:18])(=[O:17])=[O:16].N1C=CC=CC=1>C(Cl)Cl>[CH3:18][S:15]([N:14]([CH3:13])[CH:19]1[CH2:20][CH2:21][N:22]([C:2]([Cl:1])=[O:4])[CH2:23][CH2:24]1)(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 20569916HCID 20569916, compound

Product 1

HCID 86628176HCID 86628176, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of carbonic acid ditrichloromethyl ester (triphosgene) (0.61 g, 2.08 mmol) in CH2Cl2 (30 mL) at −78° C., was added a solution of N-Methyl-N-piperidin-4-yl-methanesulfonamide (preparation described in the patent GB2000136) (1.00 g, 5.20 mmol) and pyridine (0.92 mL, 11.4 mmol) in CH2Cl2 (20 mL) over 1 hour. The temperature was raised to RT, and stirring was continued over night. The organic phase was washed with H2O, dried over Na2SO4. Concentration under vacuo yielded 0.53 g (40%) of the title compound as a light yellow solid.

Workup

  1. custompreparation
  2. customover 1 hour
  3. waitwas continued over night
  4. washThe organic phase was washed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration under vacuo

Sources & evidence

ORD record
ord-937fa38bb569439eb786669d83092eb5
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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