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

HRID 1005539Notes

Reaction equation

HRID 1005539 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.[C:22]([CH:26]1[CH2:31][CH2:30][C:29](OC)(OC)[CH2:28][CH2:27]1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([CH:26]1[CH2:31][CH2:30][C:29]([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)=[CH:28][CH2:27]1)([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 4740102-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanolHCID 109215474-Tert-butyl-1,1-dimethoxycyclohexane

Product 1

HCID 187920512-[2-(4-tert-Butylcyclohexen-1-yloxyl)ethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazoleYield 70%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the enol ether with 4-tert-butyl-1,1-dimethoxycyclohexane (1 g, 5 mmol) in the same manner as the example 41 to give the compound 50 (337 mg, 70%). Mp 99.5-100.5° C. PMR (CDCl3 -0.1% d5 -Py): δH0.86 (9 H, s, t-Bu), 1.24 (6 H, d, J 4.4 Hz, (CH3)2C), 3.12 (2 H, t, J 4.2 Hz, CH2 -Im), 3.12 (1 H, m, (CH3)2CH), 3.50 (3 H, s, NCH3), 3.97 (2 H, m, OCH2), 4.61 (1 H, m, =CH), 6.77 (2 H, d, J 1 Hz, arom-H), 7.09 (1 H, t-like, arom-H). Elementary analysis (for C25H34N2Ocl2S) Calcd. : C, 62.35% H, 7.12% N, 5.82% S, 6.66% Cl, 14.72% Found: C, 62.56% H, 7.13% N, 5.76% S, 6.57% Cl, 14.43%

Sources & evidence

ORD record
ord-2b747d97306e432a8175ccdbfaff222e
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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