2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol → 2-[2-(Cyclodecen-1-yloxyl)ethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole

HRID 1005537Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][CH2:17][OH:18])=[N:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO[C:24]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1>>[C:24]1([O:18][CH2:17][CH2:16][C:13]2[N:14]([CH3:15])[C:10]([S:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)=[C:11]([CH:19]([CH3:21])[CH3:20])[N:12]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1

Participants

Reactant 2

HCID 4740102-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol

HCID 5227021-Methoxycyclodecene

Product 1

HCID 541537672-[2-(Cyclodecen-1-yloxyl)ethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazoleYield 89.7%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the enol ether with 1-methoxycyclodecene (841 mg, 5 mmol) in the same manner as the example 41 to give the compound 48 (432 mg, 89%). Mp 94-96° C. PMR (CDCl3 -0.1% d5 -Py): δH1.24 (6 H, d, J 6.6 Hz, (CH3)2C), 3.13 (2 H, t, J 6.2 Hz, CH2 -Im), 3.10 (1 H, m, (CH3)2CH), 3.52 (3 H, s, NCH3), 4.01 (2 H, t, J 6.2 Hz, OCH2), 4.38(1 H, t, J 8.4 Hz, =CH), 6.80 (2 H, d, J 1.6 Hz, arom-H), 7.10 (1 H, t-like, arom-H). IR(KBr)cm-1 : 3436, 3035, 1660, 1567, 1558, 1471, 1408, 1376, 1237, 1104. Elementary analysis (for C25H34N2Ocl2S) Calcd. : C, 62.36% H, 7.12% N, 5.82% S, 6.66% Cl, 14.73% Found: C, 62.54% H, 7.18% N, 5.69% S, 6.60% Cl, 14.52%

Sources & evidence

ORD record: ord-0c730efc8ad14eb1b41681fce1d33e33
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06054591

Reaction notes

Loading…