2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol → HCID 18791985, compound

HRID 1005540Notes

Reaction equation

HRID 1005540 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.CO[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH:25]=1>>[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[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:24][CH2:25][CH: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 108774191-Methoxy-3,4-dihydronaphthalene

Product 1

HCID 18791985HCID 18791985, compoundYield 47.8%

Procedure

The compound 22 (345 mg, 1 mmol) was converted to the enol ether with 1-methoxy-3,4-dihydronaphthalene (801 mg, 10 mmol) in the same manner as the example 41 to give the compound 51 (226 mg, 47.8%). Mp 99-102° C. PMR (CDCl3 -0.1% d5 -Py): δH1.26 (6 H, d, J 7 Hz, (CH3)2C), 2.73 (2 H, t, J 7.8 Hz, =-CH2), 3.27 (2 H, t, J 6.2 Hz, CH2 -Im), 3.11 (1 H, m, (CH3)2CH), 3.54 (3 H, s, NCH3), 4.22 (2 H, t, J 6.2 Hz, OCH2), 5.04 (1 H, t, J 6.4 Hz, =CH), 6.79 (2 H, d, J 1.6 Hz, arom-H), 7.4-7.0 (5 H, m, arom-H) IR(KBr)cm-1 : 3434, 3060, 1636, 1566, 1252, 1099. Elementary analysis (for C25H26N2Ocl2S) Calcd. : C, 63.42% H, 5.53% N, 5.92% S, 6.77% Cl, 14.98% Found: C, 64.13% H, 5.74% N, 5.74% S, 6.62% Cl, 14.11%

Sources & evidence

ORD record
ord-0a2b82d8b9d94f2bad62d36810c50988
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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