1,3,5-Trioxane → HCID 13011650, compound

HRID 1776173Notes

Reaction equation

HRID 1776173 reaction equation
[C:1]1([CH2:7][S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1COCO[CH2:13]1>ClC(Cl)C>[CH2:7]1[S:8](=[O:9])(=[O:10])[NH:11][CH2:13][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]1=2

Participants

4

Reactant 2

HCID 80811,3,5-TrioxaneHCID 78318Benzenemethanesulfonamide

Product 1

HCID 13011650HCID 13011650, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared according to the method described in Bravo, R. D. et al. Synth. Commun. 2002, 32, 3675. A flask was charged with alpha-toluenesulfonamide (1 g, 5.8 mmol) and 1,3,5-trioxane (0.175 g, 1.9 mmol) in anhydrous dichloroethane (23 mL) and amberlyst 15H+ resin (3.7 g). The mixture was stirred at 80° C. overnight, after which the resin was filtered off and washed with methylene chloride. The organic solution was concentrated to afford a white solid (0.848 g, 79%). 1H NMR (d6-DMSO, 300 MHz) δ 7.41-7.37 (t, 1H, J=6.8 Hz), 7.30-7.24 (m, 2H), 7.19-7.16 (m, 1H), 7.12-7.09 (m, 1H), 4.42-4.40 (d, 2H, J=6.6 Hz), 4.35 (s, 2H).

Workup

  1. filtrationafter which the resin was filtered off
  2. washwashed with methylene chloride
  3. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-e6aff166963a464a88135744e984154e
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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