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

HRID 1523676Notes

Reaction equation

HRID 1523676 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-f9fcf7b7f4b64c358e58f835b679e715
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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