N-Formylmorpholine → Morpholinium, 4-(chloromethylene)-, chloride

HRID 1589252Notes

Reaction equation

HRID 1589252 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)=O.C(Cl)(=O)C([Cl:12])=O>C(OCC)C.CCCCCC>[Cl-:12].[Cl:12][CH:1]=[N+:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 20417N-FormylmorpholineHCID 65578Oxalyl chloride

Product 1

HCID 11355716Morpholinium, 4-(chloromethylene)-, chlorideYield 183%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

Under dry nitrogen, a solution of N-formyl morpholine (50.6 gm) 440 mmol) in anhydrous diethyl ether (300 ml), stirring rapidly in an ice bath is treated dropwise with a solution of oxalyl chloride (50.8 gm, 400 mmol) in hexane (30 ml). After warming to room temperature for 30 minutes, the solid product is filtered off under dry nitrogen and dried in vacuum to give 91.5% (62.2 gm, 366 mmol) of N-(chloromethylene)-morpholinium chloride.

Workup

  1. filtrationthe solid product is filtered off under dry nitrogen
  2. customdried in vacuum

Sources & evidence

ORD record
ord-471ab91a57f4481884be10e2e878d899
Source dataset
uspto-grants-1986_02
Patent number
US04568741

Reaction notes

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