Dimethylformamide → HCID 86631488, compound

HRID 911081Notes

Reaction equation

HRID 911081 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH:6]=[N:7][OH:8].CN(C=O)C.[Cl:14]N1C(=O)CCC1=O>[Cl-].[Na+].O>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6](=[N:7][OH:8])[Cl:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 82839928HCID 82839928, compound

Product 1

HCID 86631488HCID 86631488, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A 250 mL round-bottomed flask was charged with tetrahydrofuran-2-carbaldehyde oxime (2.0 g, 17 mmol) and DMF (100 mL). 1-Chloropyrrolidine-2,5-dione (2.3 g, 17 mmol) was added and stirred at ambient temperature overnight. The reaction was poured into 1:1 brine:water (800 mL) and extracted with EtOAc). The organic layer was washed with water, dried over sodium sulfate, filtered and concentrated to afford tetrahydrofuran-2-carbonyl chloride oxime (2.6 g, 100%).

Workup

  1. extractionwater (800 mL) and extracted with EtOAc)
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-558a34abd08a4dabb434966da834be41
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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