Water → HCID 13157368, compound

HRID 1721985Notes

Reaction equation

HRID 1721985 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11](C3SC=CC=3)[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].CS(O)(=O)=O.C[C:26]1(C)[O:30][CH:29]([CH2:31]O)CO1.O>CN(C)C=O>[NH:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:31][CH:29]2[O:30][CH2:26]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76519763HCID 76519763, compoundHCID 178515900HCID 178515900, compound

Product 1

HCID 13157368HCID 13157368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

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 (3X), dried, and the solvent is evaporated under reduced pressure to yield crude (II) (14.22 g) which is used without further purification.

Workup

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

Sources & evidence

ORD record
ord-e1f836967c264857a4c434e704784d95
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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