Water → HCID 86638034, compound

HRID 553399Notes

Reaction equation

HRID 553399 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][O:6][C:5](=[S:8])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)[CH2:3]1.[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][N:4]1[CH2:3][C:2]([CH3:19])([CH3:1])[CH2:7][O:6][C:5]1=[S:8]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86638033HCID 86638033, compound

Product 1

HCID 86638034HCID 86638034, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

5,5-Dimethyl-3-(2-nitrobenzyl)-[1,3]-oxazinan-2-thione (1.06 g, 3.79 mmol), iron powder (1.06 g, 19.0 mmol), ammonium chloride (0.10 g, 1.87 mmol) were suspended in ethanol (20 ml) and water (10 ml) and heated to reflux for one hour. After cooling to room temperature, the reaction mixture was filtered with suction and 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 to obtain 3-(2-aminobenzyl)-5,5-dimethyl-[1,3]-oxazinan-2-thione (0.60 g).

Workup

  1. temperatureto reflux for one hour
  2. filtrationthe reaction mixture was filtered with suction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3d9c03ae6eaf484aa6d10801236b1507
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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