Formamidine acetate → HCID 70926496, compound

HRID 1042397Notes

Reaction equation

HRID 1042397 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:9]([CH3:13])([CH3:12])[CH:8]([CH3:14])[CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[C:4](=O)[CH2:3]1.[C:18](O)(=O)C.[CH:22]([NH2:24])=[NH:23]>C(O)CCC>[CH3:1][CH:2]1[CH2:11][C:10]2[C:9]([CH3:13])([CH3:12])[CH:8]([CH3:14])[CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[C:4]2[N:24]=[CH:22][N:23]=[CH:18][C:3]1=2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 70926989HCID 70926989, compound

Product 1

HCID 70926496HCID 70926496, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 3,5,5,6,8,8-hexamethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one (prepared as described in U.S. Pat. No. 3,927,083) (10 g, 0.042 mol), formamidine acetate (21 g, 0.2 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 5,7,7,8,10,10-hexamethyl-5,6,7,8,9,10-hexahydro-benzo[h]quinazoline (˜5 g) is obtained.

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

Sources & evidence

ORD record
ord-6c5e34b5957e4b388b149e47d5a75a62
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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