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

HRID 1005527Notes

Reaction equation

HRID 1005527 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.[CH2:22]([O:26][C:27]1(OCCCC)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:23][CH2:24][CH3:25]>>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][CH2:17][O:18][C:27]3([O:26][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[N:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 4740102-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanolHCID 187919731,1-Di-n-butoxycycloheptane

Product 1

HCID 187919765-(3,5-Dichlorophenylthio)-4-isopropyl-2-[2-(1-n-butoxycycloheptyloxy)ethyl]-1-methyl-1H-imidazoleYield 20.8%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the acetal with 1,1-di-n-butoxycycloheptane (2.42 g, 10 mmol) in the same manner as the example 20 to give the compound 29 (107 mg, 20.8%). PMR (CDCl3 -0.1% d5 -Py): δH 0.90 (3 H, t, J 7.4 Hz, CH3) 1.24 (6H, d, J 7Hz, (CH3)2C), 3.00 (2H, t, J 6Hz, CH2 -Im), 3.11 (3 H, m, OCH2CH3, (CH3)2CH), 3.52(3 H, s, NCH3), 3.71 (2 H, t, J 6 Hz, OCH2), 6.83 (2 H, d, J 1.6 Hz, arom-H), 7.12 (t-like, arom-H). Elementary analysis (for C26H38N2O2Cl2S) Calcd. : C, 60.80% H, 7.46% N, 5.46% Found: C, 60.99% H, 6.56% N, 5.41%

Sources & evidence

ORD record
ord-fb4fb82c552a4e48baf0ee708cb3c2ee
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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