Ethanol → 5,6,7,8-Tetrahydroquinazoline-2,4(1H,3H)-dione

HRID 711646Notes

Reaction equation

HRID 711646 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]#[N:9].[NH2:10][C:11](N)=[O:12].CC[OH:16]>Cl>[NH:10]1[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:8](=[O:16])[NH:9][C:11]1=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 1176UreaHCID 2202972-Oxocyclohexanecarbonitrile

Product 1

HCID 4718725,6,7,8-Tetrahydroquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-oxocyclohexanecarbonitrile (615 mg, 5.0 mmol) and urea (600 mg, 10.0 mmol) in 1.25 N HCl in EtOH (20 mL) was refluxed over night. After it was cooled down to 0° C., the precipitation was collected by filtration, washed with EtOH/H2O, and dried under vacuum overnight to give the product as a white solid. 1H NMR (400 MHz, CD3OD) δ 1.67-1.80 (m, 4H), 2.25-2.29 (m, 2H), 2.38-2.42 (m, 2H). MS 167 (MH+).

Workup

  1. customthe precipitation
  2. filtrationwas collected by filtration
  3. washwashed with EtOH/H2O
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-58f5912d540547dbb60f8d5e8df02485
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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