2-tert-Butylcyclohexanone → HCID 86673207, compound

HRID 1042401Notes

Reaction equation

HRID 1042401 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)([CH3:4])([CH3:3])[CH3:2].[C:12](O)(=O)C.[CH:16]([NH2:18])=[NH:17]>C(O)CCC>[C:1]([CH:5]1[C:6]2[N:18]=[CH:16][N:17]=[CH:12][C:7]=2[CH2:8][CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1026812-tert-ButylcyclohexanoneHCID 160693Formamidine acetate

Product 1

HCID 86673207HCID 86673207, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 2-tert-butyl-cyclohexanone (10 g, 0.07 mol), formamidine acetate (40 g, 0.4 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 8-tert-butyl-5,6,7,8-tetrahydro-quinazoline (˜5 g) is obtained.

Workup

  1. customA 100 mL reaction flask
  2. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  3. customButanol is recovered by roto-evaporation
  4. customThe crude product is further purified with liquid chromatography (Biotage® system)
  5. customcrystallized

Sources & evidence

ORD record
ord-5aa36d03d77f4a0494b0c69d5ea0b35e
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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