2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol → HCID 18792021, compound

HRID 1005526Notes

Reaction equation

HRID 1005526 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(OCC(C)C)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH:23]([CH3:25])[CH3:24]>>[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][CH:23]([CH3:25])[CH3:24])[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 18791968HCID 18791968, compound

Product 1

HCID 18792021HCID 18792021, compoundYield 46%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the acetal with 1,1-diisobutoxycycloheptane (2.42 g, 10 mmol) in the same manner as the example 20 to give the compound 28 (234 mg, 46%). Rf 0.31 (Al2O3 type E, hexane-EtOAc (10:1)) PMR (CDCl3 -0.1% d5 -Py): δH0.87 (6 H, d, J 6.6 Hz, CH3) 1.24 (6 H, d, J 6.6 Hz, (CH3)2C), 1.30-1.75 (13 H, m, --CH2 --), 3.00 (2 H, t, J 6.2 Hz, CH2 -Im), 3.10 (1 H, sep, J 6.6 Hz, (CH3)2CH), 3.17 (2 H, t, J 6.6 Hz), 3.51 (3 H, s, NCH3), 3.70 (2 H, t, J 6.2 Hz, OCH2), 6.81 (2 H, d, J 1.6 Hz, arom-H), 7.12 (1 H, t, J 1.6 Hz, arom-H) Elementary analysis (for C26H38N2O2Cl2S) Cacld.: C, 60.81% H, 7.46% N, 5.45% S, 6.24% Cl, 13.81% Found: C, 61.34% H, 7.69% N, 5.33% S, 6.10% Cl, 13.42%

Sources & evidence

ORD record
ord-39fcf367e68149d6a1984b99bdabfbfa
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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