2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol → HCID 18792045, compound

HRID 1005530Notes

Reaction equation

HRID 1005530 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[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH: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])[CH2:34][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 53679932HCID 53679932, compound

Product 1

HCID 18792045HCID 18792045, compoundYield 38.5%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the acetal with 1-n-butoxycyclooctene (1.3 g, 5.56 mmol) in the same manner as the example 20 to give the compound 32 (203 mg, 38%). Rf 0.70 (Al2O3 hexane-EtOAc 4:1) PMR (CDCl3 -0.1% d5 -Py): δH0.88 (3 H, t, J 7.2 Hz, CH3), 1.23 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.25-1.80 (14 H, m, --CH2 --), 2.99 (2 H, t, J 5.7 Hz, CH2 -Im), 3.05 (2 H, t, J 6.6 Hz, CH2 -Im), 3.10 (1 H, s, J 6.9 Hz, (CH3)2CH), 3.51 (3 H, s, NCH3), 3.67 (2 H, t, J 6 Hz, OCH2), 6.82 (2 H, d, J 1.8 Hz, arom-H), 7.12 (1 H, t-like, arom-H) Elementary analysis (for C27H40N2O2Cl2S) Calcd.: C, 61.47% H, 7.64% N, 5.31% S, 6.08% Cl, 13.44% Found: C, 61.58% H, 7.71% N, 5.36% S, 6.16% Cl, 13.18%

Sources & evidence

ORD record
ord-b583a85b782243bfafd20e66b2c26c27
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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