Chlorosuccinimide → HCID 86644167, compound

HRID 1511159Notes

Reaction equation

HRID 1511159 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@:5]([CH3:10])([CH:7]=[N:8][OH:9])[CH2:4][O:3]1.[Cl:12]N1C(=O)CCC1=O>CN(C=O)C.O>[OH:9][N:8]=[C:7]([Cl:12])[C@:5]1([CH3:10])[CH2:4][O:3][C:2]([CH3:11])([CH3:1])[O:6]1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 86644166HCID 86644166, compound

Product 1

HCID 86644167HCID 86644167, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(R)-2,2,4-Trimethyl-1,3-dioxolane-4-carbaldehyde oxime (4.8 g, 30 mmol) was dissolved in DMF (100 mL) and 1-chloropyrrolidine-2,5-dione (4.0 g, 30 mmol) was added. The reaction was stirred at ambient temperature overnight, then poured in water (600 mL) with of stirring. After 15 minutes the cloudy suspension was extracted with EtOAc and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated to afford (S)-N-hydroxy-2,2,4-trimethyl-1,3-dioxolane-4-carbimidoyl chloride (5.5 g, 28 mmol, 94% yield).

Workup

  1. stirringof stirring
  2. extractionAfter 15 minutes the cloudy suspension was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25afa624853b4a989c3751f3fbf9c85b
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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