Water → (S)-N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride

HRID 1511139Notes

Reaction equation

HRID 1511139 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH:7]=[N:8][OH:9])[CH2:4][O:3]1.[Cl:11]N1C(=O)CCC1=O.CCOCC.O>CN(C=O)C>[OH:9][N:8]=[C:7]([Cl:11])[C@@H:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 86644159(R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime

Product 1

HCID 86644160(S)-N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chlorideYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime (10.3 g, 71.0 mmol) in 40 mL DMF was added 1-chloropyrrolidine-2,5-dione (10.4 g, 78.1 mmol) and the reaction was stirred overnight at ambient temperature. The reaction mixture was poured into ether (1400 mL) and water (500 mL). The ether layer was extracted with water (5×500 mL), dried over MgSO4, filtered and concentrated to (S)-N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride (10.0 g, 55.7 mmol, 78.5% yield) as white solid.

Workup

  1. extractionThe ether layer was extracted with water (5×500 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c06f8ab564924896bb91beb541856cda
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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