N-methyl-2-pyrrolidone → HCID 59710620, compound

HRID 2221123Notes

Reaction equation

HRID 2221123 reaction equation
[C:1]([S:20][CH2:21][CH2:22][NH:23][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1[C:37](=[O:38])CCC1.[S:39](Cl)([CH3:42])(=[O:41])=[O:40]>C1COCC1>[C:1]([S:20][CH2:21][CH2:22][NH:23][C:24]([C:25]1[CH:30]=[CH:29][C:28]([CH2:37][O:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:27][CH:26]=1)=[O:31])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 31297Methanesulfonyl chlorideHCID 25214145HCID 25214145, compound

Product 1

HCID 59710620HCID 59710620, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl)-N-[2-(tritylsulphanyl)ethyl]benzamide (226 mg, 0.500 mmol) in dry THF (8 ml) was added N-methyl pyrrolidinone (NMP) (61 μl, 0.55 mmol) and mesyl chloride (85 μl, 1.1 mmol). The reaction mixture was stirred at room temperature for 48 hours, filtered through silica and concentrated. The product was purified by column chromatography (silica, 1% methanol in chloroform) to give 213 mg of an oil that solidified slowly. NMR analysis was in accordance with the structure.

Workup

  1. filtrationfiltered through silica
  2. concentrationconcentrated
  3. customThe product was purified by column chromatography (silica, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-51b69ee231c6448cbee3cdb144ca2c15
Source dataset
uspto-grants-2008_05
Patent number
US07368474B2

Reaction notes

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