Sodium Methoxide → HCID 86702157, compound

HRID 1776235Notes

Reaction equation

HRID 1776235 reaction equation
[S:1]1(=[O:7])(=[O:6])[CH:5]=[CH:4][CH2:3][NH:2]1.[CH3:8][O-:9].[Na+]>CO>[CH3:8][O:9][CH:4]1[CH2:5][S:1](=[O:7])(=[O:6])[NH:2][CH2:3]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 154184022,3-Dihydro-1H-1lambda~6~,2-thiazole-1,1-dione

Product 1

HCID 86702157HCID 86702157, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 2,3-dihydroisothiazole-1,1-dioxide (0.100 g, 0.8 mmol) in methanol (1 mL) was added 25% sodium methoxide in methanol (0.181 g, 0.8 mmol) and the solution stirred at 60° C. for 2 hrs and at 70° C. for 3 hrs. The mixture was concentrated and suspended in 1 N aqueous hydrochloric acid. The aqueous mixture was extracted with ethyl acetate (3×), and the organic layers dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-6% methanol/methylene chloride) to give the product (0.011 g, 13%). 1H NMR (300 MHz, CDCl3) δ 4.53 (br s, 1H), 4.33-4.29 (m, 1H), 3.48-3.30 (m, 3H), 3.37 (s, 3H), 3.19-3.13 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 80.8, 57.1, 53.3, 48.7.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×)
  3. dry with materialthe organic layers dried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography (0-6% methanol/methylene chloride)

Sources & evidence

ORD record
ord-e0a048b3da244934a3e4d261f3b9740e
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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