2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol → HCID 18791980, compound

HRID 1005529Notes

Reaction equation

HRID 1005529 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:24][C:25]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1)[CH3:23]>>[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:25]3([O:24][CH2:22][CH3:23])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]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 54569061HCID 54569061, compound

Product 1

HCID 18791980HCID 18791980, compoundYield 46.4%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the acetal with 1-ethoxycyclooctene (1.61 g, 10 mmol) in the same manner as the example 20 to give the compound 31 (232 mg, 46%). Rf 0.54 (Al2O3 hexane-EtOAc 4:1) PMR (CDCl3 -0.1% d5 -Py): δH1.06 (3 H, d, J 7 Hz), 1.37-1.80 (14 H, m), 3.00 (2 H, t, J 6 Hz, CH2 -Im), 3.00 (2 H, t, J 6 Hz, CH2 -Im), 3.07 (2 H, q, J 7 Hz, OCH2), 3.10 (1 H, s, J 7 Hz, (CH3)2CH), 3.51 (3 H, s, NCH.3), 3.68 (2 H, t, J 6.2 Hz, OCH2), 6.82 (2 H, d, J 1.8 Hz, arom-H), 7.11 (1 H, t-like, arom-H) Elementary analysis (for C25H36N2O2Cl2S) Calcd. : C, 60.11% H, 7.26% N, 5.61% S, 6.42% Cl, 14.19% Found: C, 59.91% H, 7.36% N, 5.74% S, 6.23% Cl, 13.88%

Sources & evidence

ORD record
ord-8f9ed70349154a31b0e546deab067443
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

Loading…