Methanesulfonyl chloride → HCID 86748040, compound

HRID 1741633Notes

Reaction equation

HRID 1741633 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[NH:18][CH3:19].C([Li])CCC.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>O1CCCC1>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[N:18]([S:26]([CH3:25])(=[O:28])=[O:27])[CH3:19]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 21847049HCID 21847049, compoundHCID 178418339Butyllithium

Product 1

HCID 86748040HCID 86748040, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of 1.33 g of 6-methyl-5-(N-methylamino)pyridine-2,3-dicarboxylic acid, diethyl ester, in 30 mL dry tetrahydrofuran is cooled under nitrogen with stirring to -65° C., and treated dropwise with 2.6 mL of 2.3M n-butyllithium (hexane solution). When the addition is complete, 0.4 mL of methanesulfonyl chloride is added, and the reaction is allowed to warm to room temperature over a 30 minute period. The reaction is quenched with 10 mL of water and concentrated in vacuo. The residue is partitioned between methylene chloride and water, and the organic layer is dried and concentrated in vacuo. This residue is chromatographed on silica gel using ether to afford the desired product, mp 90°-93° C.

Workup

  1. additionWhen the addition
  2. temperatureto warm to room temperature over a 30 minute period
  3. customThe reaction is quenched with 10 mL of water
  4. concentrationconcentrated in vacuo
  5. customThe residue is partitioned between methylene chloride and water
  6. customthe organic layer is dried
  7. concentrationconcentrated in vacuo
  8. customThis residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-a2f07e95bba242fdb11a1949bc718252
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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