Potassium Hydroxide → 2-Amino-6,7-dihydro-7-phenylcyclopent(e)-1,3-oxazin-4(5H)-one

HRID 474251Notes

Reaction equation

HRID 474251 reaction equation
S(O)(O)(=O)=O.CS[C:8](=[NH:10])[NH2:9].[OH-].[K+].[O:13]=[C:14]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH:15]1[C:25](OCC)=[O:26]>O>[NH2:9][C:8]1[O:13][C:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][CH2:16][C:15]=2[C:25](=[O:26])[N:10]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 10561546Ethyl 2-oxo-3-phenylcyclopentanecarboxylate

Product 1

HCID 53236142-Amino-6,7-dihydro-7-phenylcyclopent(e)-1,3-oxazin-4(5H)-oneYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methyl-2-thiopseudourea sulfate (1.336 g, 9.61 mmol) was dissolved in water (10 mL) and KOH (1.128 g, 20.10 mmol) was added. While stirring, ethyl 2-oxo-3-phenylcyclopentanecarboxylate (2.03 g, 8.74 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, washed with water and ether, and dried over anhydrous sodium sulfate to afford 2-amino-7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazin-4(5H)-one (1.22 g, 5.35 mmol, 61.2% yield) as white solid. LC-MS (M+H)+=229.1. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.57-7.85 (2H, m), 7.08-7.47 (5H, m), 4.25-4.38 (1H, m), 1.72-2.73 (3H, m), 1.09-1.31 (1H, m).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. washwashed with water and ether
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-a304d809731d4e3b861941eb0e255d89
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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