(+-)-Cashmeran → 5H-Cyclopenta[h]quinazoline, 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-

HRID 2369769Notes

Reaction equation

HRID 2369769 reaction equation
[CH3:1][CH:2]1[C:6]([CH3:8])([CH3:7])[C:5]2[C:9]([CH2:11][CH2:12][CH2:13][C:4]=2[C:3]1([CH3:15])[CH3:14])=O.[C:16](O)(=O)C.[CH:20]([NH2:22])=[NH:21]>C(O)CCC>[CH3:14][C:3]1([CH3:15])[C:4]2[CH2:13][CH2:12][C:11]3[CH:16]=[N:21][CH:20]=[N:22][C:9]=3[C:5]=2[C:6]([CH3:8])([CH3:7])[CH:2]1[CH3:1]

Participants

4

Reactant 2

HCID 92292(+-)-CashmeranHCID 160693Formamidine acetate

Product 1

HCID 681623655H-Cyclopenta[h]quinazoline, 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
118 °C

Procedure

A 5 L reaction vessel was charged with Cashmeran™ (412 g, 2.0 mol, commercially available at IFF), formamidine acetate (1030 g, 10.0 mol), and butanol (1.2 L). The reaction mixture was heated to 118° C. for 4 hours and then cooled to 25° C. The reaction mixture was washed twice with brine (1 L) and purified by vacuum distillation to afford 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline (260 g) having a boiling point of 140° C. at a pressure of 1.6 mmHg Further recrystallization from ethanol afforded a solid with a melting point of 80.0° C.

Workup

  1. customA 5 L reaction vessel
  2. temperaturecooled to 25° C
  3. washThe reaction mixture was washed twice with brine (1 L)
  4. distillationpurified by vacuum distillation

Sources & evidence

ORD record
ord-90cbc68414264505976542f7f11c984b
Source dataset
uspto-grants-2014_04
Patent number
US08709993B2

Reaction notes

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