Water → HCID 178521466, compound

HRID 235938Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].CS(O)(=O)=O.[CH3:25][C:26]1([CH3:33])[O:30][CH:29]([CH2:31][OH:32])[CH2:28][O:27]1.O>CN(C)C=O>[CH2-:3][C:2]([CH3:7])=[O:1].[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:33][C:26]([O:27][CH2:28][CH:29]([OH:30])[CH2:31][OH:32])=[CH:25][CH:4]=2)[NH:9][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(p-hydroxyphenyl)-4-(2-thienyl)imidazole (19.5 g, 0.08 m) in dimethylformamide (65 ml) is added to a stirred suspension of sodium hydride (4.8 g, 0.10 m, 50% dispersion in mineral oil) in dimethylformamide (20 ml) at 80° C. After stirring at 80° C. for 0.5 hours, a solution of 2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane methanesulfonate, (I) (16.82 g, 0.08 m) in dimethylformamide (20 ml) is added rapidly and the mixture is stirred under nitrogen at 80° C. for 17 hours. The reaction mixture is poured into H2O (400 ml) and extracted with ether (3×350 ml). The combined extracts are washed with 5% NaOH solution (2×250 ml) and with H2O (3×), dried, and the solvent is evaporated under reduced pressure to yield crude (II) (14.22 g) which is used without further purification.

Workup

stirringthe mixture is stirred under nitrogen at 80° C. for 17 hours
extractionextracted with ether (3×350 ml)
washThe combined extracts are washed with 5% NaOH solution (2×250 ml) and with H2O (3×)
customdried
customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record: ord-06cc16638b7241fabcd1e6cbf8bba810
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642311

Reaction notes

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