Formamidine acetate → HCID 70926312, compound

HRID 1042396Notes

Reaction equation

HRID 1042396 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[C:7](=O)[CH2:6][CH2:5][CH2:4][C:3]1=2.[C:16](O)(=O)C.[CH:20]([NH2:22])=[NH:21]>C(O)CCC>[CH3:1][C:2]1([CH3:15])[C:3]2[CH2:4][CH2:5][C:6]3[CH:16]=[N:21][CH:20]=[N:22][C:7]=3[C:8]=2[C:9]([CH3:13])([CH3:12])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 70926216HCID 70926216, compound

Product 1

HCID 70926312HCID 70926312, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 5,5,8,8-tetramethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one (prepared as described in U.S. Pat. Nos. 3,927,083 and 2,912,462) (10 g, 0.048 mol), formamidine acetate (25 g, 0.24 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 7,7,10,10-tetramethyl-5,6,7,8,9,10-hexahydro-benzo[h]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-25480c98b5eb49ee84cd63ddf4f60b33
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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