Chlorosuccinimide → HCID 86644164, compound

HRID 1523689Notes

Reaction equation

HRID 1523689 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 86644163HCID 86644163, compound

Product 1

HCID 86644164HCID 86644164, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-2,2,4-Trimethyl-1,3-dioxolane-4-carbaldehyde oxime (5.7 g, 36 mmol) was dissolved in DMF (120 mL) and 1-chloropyrrolidine-2,5-dione (4.8 g, 36 mmol) was added. The reaction was stirred at ambient temperature overnight, and then poured in water (600 mL) with stirring. After 15 minutes the cloudy suspension was extracted with EtOAc, washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford (R)—N-hydroxy-2,2,4-trimethyl-1,3-dioxolane-4-carbimidoyl chloride (6.4 g, 33 mmol, 92% yield).

Workup

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

Sources & evidence

ORD record
ord-2025b855da904a91a6f84cf338bd6523
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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