4-tert-Butylcyclohexanone → HCID 484964, compound

HRID 727158Notes

Reaction equation

HRID 727158 reaction equation
[CH3:1][C:2]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])[CH3:3].[C:12]([NH:14][C:15]([NH2:17])=[NH:16])#[N:13]>C(OCCOCCO)C>[NH2:17][C:15]1[N:14]=[C:12]([NH2:13])[C:9]2[CH2:10][CH:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH2:6][CH2:7][C:8]=2[N:16]=1

Participants

4

Reactant 2

HCID 73924-tert-ButylcyclohexanoneHCID 178418324HCID 178418324, compound

Product 1

HCID 484964HCID 484964, compound

Reagents, catalysts & solvents 1

HCID 8146Diethylene Glycol Monoethyl EtherSolvent

Conditions

Temperature
160 °C

Procedure

A reaction vessel equipped with a Dean Stark trap was charged with 11.8 grams (0.075 mole) of 4-(1,1-dimethylethyl)cyclohexanone and 4.2 grams (0.050 mole) of cyanoguanidine in 20 mL of 2-(2-ethoxyethoxy)ethanol. The mixture was heated incrementally at 80° C., 100° C., 140° C. and 160° C., the latter where it was stirred for about 18 hours. The reaction mixture was then cooled to ambient temperature, where it solidified. The reaction mixture was triturated with 30 mL of diethyl ether, and the resultant solid was collected by filtration. The solid was washed several times with diethyl ether, yielding, when dried, 4.5 grams of 2,4-diamino-6-(1,1-dimethylethyl)-5,6,7,8-tetrahydroquinazoline, mp>250° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customA reaction vessel equipped with a Dean Stark trap
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. customThe reaction mixture was triturated with 30 mL of diethyl ether
  4. filtrationthe resultant solid was collected by filtration
  5. washThe solid was washed several times with diethyl ether
  6. customyielding
  7. customwhen dried

Sources & evidence

ORD record
ord-fe2e8bd1ce8c427f9b0a792d3354d240
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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