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

HRID 451019Notes

Reaction equation

HRID 451019 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. Under 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, dimethylsulfoxide-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-a8da8d00d6ec4054b13e064f1e9b1b2a
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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