3-Chloro-6-ethyl-4-hydroxy-6-methyl-5,6-dihydro-pyran-2-one → 3-(5-Chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-ethyl-4-hydroxy-6-methyl-5,6-dihydro-pyran-2-one

HRID 1453258Notes

Reaction equation

HRID 1453258 reaction equation
Cl[C:2]1[C:3](=[O:12])[O:4][C:5]([CH2:10][CH3:11])([CH3:9])[CH2:6][C:7]=1[OH:8].[Cl:13][C:14]1[CH:26]=[CH:25][C:17]2[N:18]([CH:22]([CH3:24])[CH3:23])[C:19]([SH:21])=[N:20][C:16]=2[CH:15]=1>>[Cl:13][C:14]1[CH:26]=[CH:25][C:17]2[N:18]([CH:22]([CH3:24])[CH3:23])[C:19]([S:21][C:2]3[C:3](=[O:12])[O:4][C:5]([CH2:10][CH3:11])([CH3:9])[CH2:6][C:7]=3[OH:8])=[N:20][C:16]=2[CH:15]=1

Participants

3

Reactant 2

HCID 587624553-Chloro-6-ethyl-4-hydroxy-6-methyl-5,6-dihydro-pyran-2-oneHCID 178456613HCID 178456613, compound

Product 1

HCID 587622953-(5-Chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-ethyl-4-hydroxy-6-methyl-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared from 3-Chloro-6-ethyl-4-hydroxy-6-methyl-5,6-dihydro-pyran-2-one (from Step 1) and 5-Chloro-1-isopropyl-1H-benzoimidazole-2-thiol using the coupling method described in Example C(4). 1H NMR (CDCl3): δ 0.95 (t, 3H, J=7.5 Hz), 1.41 (s, 3H), 1.68 (d, 6H, J=7.0 Hz), 1.75 (m, 2H), 2.52 (d, 1H, J=17.1 Hz), 2.74 (d, 1H, J=17.1 Hz), 6.97 (m, 1H), 6.56 (br s, 1H), 7.28 (d, 1H, J=8.9 Hz), 7.48 (d, 1H, J=8.9 Hz), 7.60 (s, 1H). Anal. Calcd. For C18H21N2O3SCl.0.1H2O: C, 56.49; H, 5.58; N, 7.32. Found: C, 56.32; H, 5.56; N, 7.17.

Sources & evidence

ORD record
ord-71ac5a3ba9e041479ad12c4e26313988
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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