Formamidine acetate → HCID 70926297, compound

HRID 1042399Notes

Reaction equation

HRID 1042399 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][CH2:9][C:8]2([CH3:12])[CH:3]1[CH2:4][CH2:5][C:6](=O)[CH2:7]2.[C:15](O)(=O)C.[CH:19]([NH2:21])=[NH:20]>C(O)CCC>[CH3:1][C:2]1([CH3:14])[CH:3]2[CH2:4][C:5]3[CH:15]=[N:20][CH:19]=[N:21][C:6]=3[CH2:7][C:8]2([CH3:12])[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 6429085HCID 6429085, compound

Product 1

HCID 70926297HCID 70926297, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 5,5,8a-trimethyl-octahydro-naphthalen-2-one (prepared as described by Strike in Journal of the American Chemical Society, 1964, 86(10), pages: 2044-2050) (10 g, 0.05 mol), formamidine acetate (27 g, 0.26 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. A mixture of products 5,7,7,8,10,10-hexamethyl-5,6,7,8,9,10-hexahydro-benzo[h]quinazoline and 6,6,9a-Trimethyl-5,5a,6,7,8,9,9a,10-octahydro-benzo[g]quinazoline (˜5 g) is obtained, which may be separated using techniques known to those having skill in the art. Suitable techniques include chromatography such as high performance liquid chromatography, referred to as HPLC, and particularly silica gel chromatography and gas chromatography trapping known as GC trapping.

Workup

  1. customA 100 mL reaction flask
  2. customprepared
  3. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  4. customButanol is recovered by roto-evaporation
  5. customThe crude product is further purified with liquid chromatography (Biotage® system)
  6. customcrystallized
  7. additionA mixture of products 5,7,7,8,10,10-hexamethyl-5,6,7,8,9,10-hexahydro-benzo[h]quinazoline

Sources & evidence

ORD record
ord-342ac230cbfe47eeb278b8539d2cac8f
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

Loading…