Ethylamine → HCID 13366431, compound

HRID 1632471Notes

Reaction equation

[CH3:1]/[C:2](/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:27])/[CH:11]=[CH:12]/[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][C:21]([F:24])([F:23])[F:22])=[C:15]([CH3:25])[C:14]=1[CH3:26])=[CH:3]\[C:4]([OH:6])=O.C(N1C=CN=C1)([N:30]1[CH:34]=[CH:33]N=C1)=O.C(N)C>C1COCC1.CCCCCC>[CH2:34]([NH:30][C:4](=[O:6])/[CH:3]=[C:2](\[CH3:1])/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:27])/[CH:11]=[CH:12]/[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][C:21]([F:22])([F:23])[F:24])=[C:15]([CH3:25])[C:14]=1[CH3:26])[CH3:33]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 2.0 g (5.3 mmol) of (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoic acid in 60 ml of dry THF and 1.6 g of (10 mmol) of carbonyldiimidazole was heated to 35°-40° C. for 0.5 hour. The reaction mixture was cooled to -10° C. and excess gaseous ethyl amine was introduced. The resulting mixture was stirred for 1 hour at 23° C., diluted with 100 ml of hexane, and filtered through silica gel (200 g, 1:1 ethyl acetate-hexane as elutant). Further chromatographic purification (silicia gel, 5 to 10% ethyl acetate in methylene chloride) gave a yellow solid which, after recrystallization (ethyl acetate-hexane), yielded 1.4 g of N-ethyl(2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenamide; mp 198°-200° C.

Workup

filtrationfiltered through silica gel (200 g, 1:1 ethyl acetate-hexane as elutant)
customFurther chromatographic purification (silicia gel, 5 to 10% ethyl acetate in methylene chloride)
customgave a yellow solid which
customafter recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record: ord-80d21e8ca0a0435db67b2b14c4971aa5
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04476056

Reaction notes

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