Dimethylformamide → HCID 86631488, compound

HRID 1806057Notes

Reaction equation

HRID 1806057 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 (500 mL). The organic layer was washed twice with water, dried over sodium sulfate, filtered and concentrated to afford the title compound (2.6 g, 100%).

Workup

  1. extractionwater (800 mL) and extracted with EtOAc (500 mL)
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d215e67c85284df9a249feff8e33e036
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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