Trichloroisocyanuric Acid → HCID 54583508, compound

HRID 1770764Notes

Reaction equation

HRID 1770764 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[O:9][C:8](=[O:10])[NH:7][C:6]([CH3:12])([CH3:11])[CH2:5]1.[Cl:13]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>ClCCl.CO>[Cl:13][N:7]1[C:6]([CH3:12])([CH3:11])[CH2:5][CH:4]([CH2:3][CH2:2][OH:1])[O:9][C:8]1=[O:10]

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 67508872HCID 67508872, compound

Product 1

HCID 54583508HCID 54583508, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-hydroxyethyl)-4,4-dimethyl-1,3-oxazinan-2-one (278 mg, 1.6 mmol) in 4 mL dichloromethane and 250 uL methanol was added trichloroisocyanuric acid (370 mg, 1.6 mmol). The reaction mixture was stirred at room temperature for 4 hours and then directly purified by column chromatography (0 to 10% methanol in dichloromethane) to give a white solid (291 mg, 1.40 mmol, 87%). 1H NMR (D2O, 400 MHz) δ 1.35 (s, 6H), 1.78-1.83 (m, 2H), 1.97-2.03 (dd, J=11.9, 14.2 Hz, 1H), 2.13-2.17 (dd, J=2.1, 14.2 Hz, 1H), 3.64-3.68 (m, 2H), 4.55-4.60 (m, 2H). 13C NMR (D2O, 100 MHz) δ 24.3, 27.9, 35.8, 41.5, 63.0, 72.5, 155.15. LRMS (ESI/APCI) m/z 208 [M+H]+.

Workup

  1. customdirectly purified by column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1aed00a1b1f842309c2a66d0528937c7
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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