2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol → 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-[2-(9-methoxy-9H-fluoren-9-yloxy)ethyl]-1-methyl-1H-imidazole

HRID 1005535Notes

Reaction equation

HRID 1005535 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.[CH3:22][O:23][C:24]1(OC)[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2>>[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:24]3([O:23][CH3:22])[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=4[C:31]4[C:36]3=[CH:35][CH:34]=[CH:33][CH:32]=4)=[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 115214539,9-Dimethoxyfluorene

Product 1

HCID 187920425-(3,5-Dichlorophenylthio)-4-isopropyl-2-[2-(9-methoxy-9H-fluoren-9-yloxy)ethyl]-1-methyl-1H-imidazoleYield 21.2%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the acetal with 9,9-dimethoxyfluorene (2.26 g, 10 mmol) in the same manner as the example 20 to give the compound 43 (114 mg, 21.2%). Mp 130-131° C. PMR (CDCl3 -0.1% d5 -Py): δH1.24 (6 H, d, J 7 Hz, (CH3)2C), 3.20 (3 H, s, CH3O), 3.02 (2 H, m, CH2 -Im), 3.11 (1 H, m, (CH3)2CH), 3.42 (3 H, s, NCH3), 3.85 (2 H, t, J 6.2 Hz, OCH2), 6.8-7.6 (8 H, m, arom-H) Elementary analysis (for C29H28N2O2Cl2S) Calcd.: C, 64.56% H, 5.23% N, 5.19% S, 5.94% Cl, 13.14% Found: C, 64.65% H, 5.25% N, 5.10% S, 5.95% Cl, 12.89%

Sources & evidence

ORD record
ord-f75aebe4fc5e44edb253518181f7fa4a
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

Loading…