Tert-Butyl hypochlorite → HCID 46202339, compound

HRID 1023496Notes

Reaction equation

HRID 1023496 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:18])[CH2:10][N:9]([CH2:11][CH2:12][N+:13]([CH3:16])([CH3:15])[CH3:14])[C:8](=[O:17])[NH:7]1.C(O[Cl:24])(C)(C)C>CO>[C:1]([O-:4])(=[O:3])[CH3:2].[Cl:24][N:7]1[C:6]([CH3:18])([CH3:5])[CH2:10][N:9]([CH2:11][CH2:12][N+:13]([CH3:16])([CH3:15])[CH3:14])[C:8]1=[O:17]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochlorite2×HCID 68563804HCID 68563804, compound

Product 1

HCID 46202339HCID 46202339, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-N,N,N-trimethylethanaminium acetate (0.428 mmol) in MeOH (2 ml) was cooled to 0° C. tert-Butylhypochlorite (100 ul, 0.84 mmol) was added, causing a white precipitate to form. The solution was stirred for 15 min, and another portion of tert-butylhypochlorite (100 ul, 0.84 mmol) was added. The solution was stirred for an additional 15 min, then concentrated in vacuo. The residue was purified by RP-HPLC (H2O/CH3CN) to afford the title compound as a white powder (74.7 mg, 0.276 mmol, 65%). 1H NMR (D2O, 400 MHz) δ 1.24 (s, 6H), 1.85 (s, 3H), 3.11 (s, 9H), 3.37 (s, 2H), 3.50 (m, 2H), 3.68 (m, 2H). 13C NMR (D2O, 100 MHz) δ 22.32, 27.01, 39.24, 55.38, 57.82, 62.40, 161.31, 180.46. ESI/APCI (pos) expected for C10H21ClN3O+: 234.14. Found: 234.

Workup

  1. additionwas added
  2. customto form
  3. stirringThe solution was stirred for an additional 15 min
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by RP-HPLC (H2O/CH3CN)

Sources & evidence

ORD record
ord-3aa4288c678145889d0e5439b82e67d7
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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