Acetic Acid → 5H-Cyclopenta[h]quinazoline, 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-

HRID 1042392Notes

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(O)(=O)C.[CH:20]([NH2:22])=[NH:21].[C:23](C)(O)=O>C(O)CCC>[CH3:7][C:6]1([CH3:8])[C:5]2[C:9]3[C:11]([CH2:12][CH2:13][C:4]=2[C:3]([CH3:15])([CH3:14])[CH:2]1[CH3:1])=[CH:23][N:22]=[CH:20][N:21]=3

Participants

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 (HN2CH═NH/HOOCCH3) (1.03 Kg, 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 1,1,2,3,3-pentamethyl-2,3,4,5-tetrahydro-1H-7,9-diaza-cyclopenta[a]naphthalene (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

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

Sources & evidence

ORD record: ord-943bba11181c41bfbe5ac4855eae8686
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557876B2

Reaction notes

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