Sodium hydride → HCID 21709131, compound

HRID 651704Notes

Reaction equation

HRID 651704 reaction equation
[C:1]([CH2:3][S:4]([NH:7][CH3:8])(=[O:6])=[O:5])#[N:2].[H-].[Na+].[CH2:11]([O:18][CH2:19]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[CH2:11]([O:18][CH2:19][N:7]([CH3:8])[S:4]([CH2:3][C:1]#[N:2])(=[O:6])=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 21709128HCID 21709128, compound

Product 1

HCID 21709131HCID 21709131, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-cyano-N-methylmethanesulfonamide (from step (b), 250 mg, 1.9 mmol) in tetrahydrofaran (5 ml) at 0-5° C. under an atmosphere of nitrogen was added sodium hydride (60% dispersion in mineral oil, 75 mg, 1.9 mmol) in one portion. The resulting slurry was stirred at 0-5° C. for 45 min, before benzyloxymethyl chloride (80% purity, 0.368 g, 1.9 mmol) in tetrahydrofuran (5 ml) was added dropwise over a 15 min period. The mixture was then allowed to warm to ambient temperature over a 3 hr period. The solvents were then evaporated in vacuo and the resulting oil was purified by flash column chromatography (diethyl ether:hexanes 3:1 as eluant) to yield the subtitle compound (296 mg, 61.6%) as a colourless oil.

Workup

  1. additionwas added dropwise over a 15 min period
  2. customThe solvents were then evaporated in vacuo
  3. customthe resulting oil was purified by flash column chromatography (diethyl ether:hexanes 3:1 as eluant)

Sources & evidence

ORD record
ord-ab00ab96c5454089a36acdfbcbbe6cdd
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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