Thioanisole → HCID 178424021, compound

HRID 1595388Notes

Reaction equation

HRID 1595388 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)=[C:18]([C:20]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[O:21])[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1.[OH-].[Na+]>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17]([C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)=[C:18]([C:20]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[O:21])[N:19]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 14798Sodium HydroxideHCID 178424022HCID 178424022, compound

Product 1

HCID 178424021HCID 178424021, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(4-Benzyloxyphenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (5.10 g) obtained in Example 22(3) and thioanisole (6.4 ml) were dissolved in trifluoroacetic acid (100 ml) and the mixture was stirred for 6 hr. The reaction mixture was made alkaline with 2 M aqueous sodium hydroxide solution and then acidified withaqueouscitricacid. Themixturewasextractedwithethylacetate. The ethyl acetate layer was washed with saturated brine and, after drying, the solvent was evaporated. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=6:4) and recrystallized from ethyl acetate and hexane to give 2-(4-hydroxyphenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (2.33 g), melting point 286-289° C. (decomposition).

Workup

  1. washThe ethyl acetate layer was washed with saturated brine
  2. customafter drying
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=6:4)
  5. customrecrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-9241daf376ed48ae99fa27384c04436a
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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