Tert-Butyl hypochlorite → HCID 86665548, compound

HRID 1770755Notes

Reaction equation

HRID 1770755 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]1([CH3:21])[CH3:20].[Cl:22]OC(C)(C)C>CO>[Cl:22][N:14]1[C:15]([CH3:19])([CH3:18])[C:16](=[O:17])[N:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:13]1([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67508105HCID 67508105, compound

Product 1

HCID 86665548HCID 86665548, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3-(2-(2-methoxyethoxy)ethoxy)propyl)-2,2,5,5-tetramethylimidazolidin-4-one (182 g, 0.60 mmol) in methanol (10 mL) was cooled in ice water for 10 minutes, before neat tert-butyl hypochlorite (0.10 mL, 0.9 mmol, 1.5 equiv.) was added in one portion. High pressure liquid chromatography-mass spectroscopy analysis after 5 minutes showed all starting amine had been consumed. After 20 min, the mixture was concentrated in vacuo to an oil, which was absorbed on silica (1 g). Chromatography on silica (0-4% methanol in dichloromethane) afforded the title compound as a colorless oil (193 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 3.66-3.62 (m, 4H), 361-3.58 (m, 2H), 3.56-3.53 (m, 2H), 3.51 (t, J=6.0 Hz, 2H), 3.38 (s, 3H), 3.35-3.30 (m, 2H), 1.96-1.88 (m, 2H), 1.45 (s, 6H), 1.33 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 172.6, 82.1, 71.9, 70.59, 70.54, 70.13, 68.6, 65.3, 59.0, 38.2, 29.1, 25.1, 23.5; LRMS (ESI/APCI) m/z 337 [M+H]+.

Workup

  1. additionwas added in one portion
  2. customall starting amine had been consumed
  3. waitAfter 20 min
  4. concentrationthe mixture was concentrated in vacuo to an oil, which
  5. customwas absorbed on silica (1 g)

Sources & evidence

ORD record
ord-c65473ed79914de2aefe36b6af6c2bca
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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