Water → HCID 68511562, compound

HRID 2189977Notes

Reaction equation

HRID 2189977 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].O>CN1C(=O)CCC1>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([N:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 68511562HCID 68511562, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of methyl 6-chloronicotinate (3.43 g, 20 mmol), thiomorpholine 1,1-dioxide (2.70 g, 20 mmol) and sodium carbonate (2.54 g, 24 mmol) in NMP (40 mL) was heated to 90° C. for 3 days. The reaction mixture was poured into water and the white solid formed was filtered off to give 2.22 g 6-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-nicotinic acid methyl ester. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over Na2SO4, filtered and the solvents were evaporated. The residue was triturated with diethyl ether and the solid filtered off to yield another 1.18 g 6-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-nicotinic acid methyl ester.

Workup

  1. customthe white solid formed
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-be1ee2e26da84fd890c2fba6b9b68690
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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