Methanesulfonyl chloride → (S)-2,2-dimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride

HRID 1523677Notes

Reaction equation

HRID 1523677 reaction equation
[OH:1][N:2]=[C:3]([Cl:11])[C@@H:4]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5]1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)C(C)C)(C)C>C1COCC1>[CH3:10][C:6]1([CH3:9])[O:5][C@H:4]([C:3]([Cl:11])=[N:2][O:1][S:13]([CH3:12])(=[O:15])=[O:14])[CH2:8][O:7]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86644160(S)-N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride

Product 1

HCID 86644161(S)-2,2-dimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chlorideYield 86.63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)—N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride (9.88 g, 55.01 mmol) in THF (200 mL) at 0° C. was added methanesulfonyl chloride (4.703 ml, 60.51 mmol), followed by N,N-diisopropylethylamine (10.54 ml, 60.51 mmol) and the reaction was stirred for 1 hour at ambient temperature, filtered and concentrated in vacuo. The residue was purified over silica gel (25 to 100% ethyl acetate in hexanes) to afford (S)-2,2-dimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (12.28 g, 47.65 mmol, 86.63% yield) as colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified over silica gel (25 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-217ed10cd0cd4f28bd56c00279d1979e
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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