Water → HCID 86638033, compound

HRID 553398Notes

Reaction equation

HRID 553398 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[CH2:3][OH:4].C(N(CC)CC)C.[C:25](Cl)(Cl)=[S:26].O>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH2:3][O:4][C:25](=[S:26])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 67461461HCID 67461461, compound

Product 1

HCID 86638033HCID 86638033, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

2,2-Dimethyl-3-(2-nitrobenzylamino)-1-propanol (1.07 g, 4.50 mmol) was dissolved in chloroform (20 ml) and the reaction solution was cooled to 0° C. Then triethylamine (1.82 g, 18.0 mmol), thiophosgene (0.52 g, 4.50 mmol) was added thereto and stirred at a temperature as is for two hours and at room temperature for one hour. The reaction mixture was added with water, stirred at room temperature for one hour and then extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 5,5-dimethyl-3-(2-nitrobenzyl)-[1,3]-oxazinan-2-thione (1.12 g).

Workup

  1. stirringstirred at room temperature for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a884f5dc890a4740bf34e54d2f5ea035
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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