Water → 4-(3-{[4-(2-methyl-1H-imidazol-1-yl)phenyl]sulfanyl}phenyl)tetrahydro-2H-pyran-4-carboxamide

HRID 636850Notes

Reaction equation

HRID 636850 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[OH-:28].[K+].O>CC(O)(C)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]([NH2:27])=[O:28])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11314856HCID 11314856, compound

Product 1

HCID 98219454-(3-{[4-(2-methyl-1H-imidazol-1-yl)phenyl]sulfanyl}phenyl)tetrahydro-2H-pyran-4-carboxamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-{3-[4-(2-Methyl-imidazol-1-yl)-phenyl sulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile (27.35 g) were dissolved in t-BuOH (280 mL) at 50° C. To the solution, KOH (12.28 g) was added and the mixture was stirred overnight. The suspension was cooled to room temperature and water (180 mL) was added. The suspension obtained was filtered and the filtercake was dried at 50° C. to yield 4-{3-[4-(2-Methyl-imidazol-1-yl)-phenyl sulfanyl]-phenyl}tetrahydro-pyran-4-carboxylic acid amide (17.52 g, 55% yield).

Workup

  1. customThe suspension obtained
  2. filtrationwas filtered
  3. customthe filtercake was dried at 50° C.

Sources & evidence

ORD record
ord-2ff0a946ca1841e8a3c6de42e029b3c3
Source dataset
uspto-grants-2001_02
Patent number
US06194585B1

Reaction notes

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