ethyl N-ethoxycarbonyliminocarbamate → 1,2-Bis(ethoxycarbonyl)-4-(4,8-dimethyl-3,7-nonadienyl)-1,2,3,6-tetrahydropyridazine

HRID 464049Notes

Reaction equation

[CH3:1][CH2:2][C:3]([CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])=[CH2:4].[N:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CCOCC>[CH2:21]([O:20][C:18]([N:17]1[CH2:1][CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])[CH2:4][N:16]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH3:22]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of the (E)-β-farnesene-containing product of Example 1 (14.5 g) in ether (20 ml) is cooled to -20° C. and diethyl azodicarboxylate (8.7 g) is slowly added with stirring. The mixture is stored at -20° C. overnight and then at 4° C., the reaction being shown by n.m.r. to be complete after 8 hours at 4° C. The mixture is then subjected to fractional distillation to give the adduct, 1,2-bis(ethoxycarbonyl)-4-(4,8-dimethyl-3,7-nonadienyl)-1,2,3,6-tetrahydropyridazine (I) as a yellow oil (8 g, 43%) 180°-185° C./0.3τ; nD20 1.4938; M+ (m/z as % of base peak): 378(2.9); δ(CCl4) 1.30 (t, 6H), 1.70 (m, 9H), 2.08 (m, 8H), 3.60-4.40 (m, 4H), 4.26 (q, 4H), 5.20 (m, 2H), 5.60 (br, t, 1H).

Workup

customat 4° C.
waitto be complete after 8 hours at 4° C
distillationThe mixture is then subjected to fractional distillation

Sources & evidence

ORD record: ord-dab080d6ec844fe6ab9b965bb712b678
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04546110

Reaction notes

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