Triethylamine → HCID 86631489, compound

HRID 911082Notes

Reaction equation

HRID 911082 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6](=[N:8][OH:9])[Cl:7].[CH3:10][S:11](Cl)(=[O:13])=[O:12].C(N(CC)CC)C>CCOCC>[CH3:10][S:11]([O:9][N:8]=[C:6]([Cl:7])[CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86631488HCID 86631488, compound

Product 1

HCID 86631489HCID 86631489, compoundYield 53.07%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 500 mL round-bottomed flask was charged with tetrahydrofuran-2-carbonyl chloride oxime (2.6 g, 17.4 mmol), methanesulfonyl chloride (1.4 ml, 17.4 mmol), and Et2O (200 mL). Triethylamine (2.4 ml, 17.4 mmol) was added dropwise over about 1 minute and stirred at ambient temperature for 10 minutes. The resultant solids were filtered and the filtrate was concentrated. The resultant residue was purified on silica gel (100% DCM) to afford N-(methylsulfonyloxy)tetrahydrofuran-2-carbimidoyl chloride (2.1 g, 53.07% yield) as a white solid.

Workup

  1. filtrationThe resultant solids were filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resultant residue was purified on silica gel (100% DCM)

Sources & evidence

ORD record
ord-a2a1464a27c04934a6d61ed4c83ad1d0
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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