Tert-Butyl hypochlorite → 1-Chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 1770728Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[NH:13][C:12]1=[O:19].C(O[Cl:25])(C)(C)C>CO>[Cl:25][N:13]1[C:14]([CH3:17])([CH3:18])[C:15](=[O:16])[N:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]1=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione (900 mg, 3.3 mmol) in methanol (80 ml) was added tert-butylhypochlorite (220 mg, 2.0 mmol). The mixture was stirred for 1 hour at 0° C. The reaction mixture was checked for completion by high pressure liquid chromatography. The reaction mixture was concentrated in vacuo, and crude material was purified by preparative-high pressure liquid chromatography to give 30 mg (3%) of the title compound. 1H NMR (D2O, 400 MHz) δ 3.79 (t, J=4.8 Hz, 2H), 3.73 (t, J=4.8 Hz, 2H), 3.69-3.58 (m, 8H), 3.37 (s, 3H), 1.49 (s, 6H); LRMS (ESI/APCI) m/z 309 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated in vacuo, and crude material
customwas purified by preparative-high pressure liquid chromatography

Sources & evidence

ORD record: ord-a39131f192d84d6081ef63fb0371f62a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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