Triethylamine → HCID 86644168, compound

HRID 534141Notes

Reaction equation

HRID 534141 reaction equation
[OH:1][N:2]=[C:3]([Cl:12])[C@:4]1([CH3:11])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>CCOCC>[CH3:10][C:6]1([CH3:9])[O:5][C@:4]([CH3:11])([C:3]([Cl:12])=[N:2][O:1][S:14]([CH3:13])(=[O:16])=[O:15])[CH2:8][O:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86644167HCID 86644167, compound

Product 1

HCID 86644168HCID 86644168, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(S)-N-hydroxy-2,2,4-trimethyl-1,3-dioxolane-4-carbimidoyl chloride (5.5 g, 28.4 mmol) was dissoved in Et2O (150 mL) and methanesulfonyl chloride (2.21 ml, 28.4 mmol) was added. Triethylamine (3.96 ml, 28.4 mmol) was added dropwise and the reaction was stirred at ambient temperature for 1 hour. The resulting solids were filtered and the filtrate concentrated. The residue was purified over silica gel (100% CH2Cl2) to afford (S)-2,2,4-trimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (4.7 g, 17.3 mmol, 60.9% yield) as an amber oil.

Workup

  1. filtrationThe resulting solids were filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified over silica gel (100% CH2Cl2)

Sources & evidence

ORD record
ord-46a0563146864afa80ef6243be49727d
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

Loading…