Ammonium Hydroxide → HCID 22129205, compound

HRID 1858432Notes

Reaction equation

HRID 1858432 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=[O:2].[K+].[K+].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[N:21]=[CH:22][N:23]([CH:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)[C:24]=1[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([S:31][CH3:32])[N:26]=1.[NH4+].[OH-]>O.CC(O)=O>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[N:21]=[CH:22][N:23]([CH:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)[C:24]=1[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([S:31]([CH3:32])=[O:2])[N:26]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24412Potassium PersulfateHCID 22464147HCID 22464147, compound

Product 1

HCID 22129205HCID 22129205, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Potassium persulfate (3.2 g, 7.0 mmol) in water (75 mL) was added to a solution of 4-(fluorophenyl)-1-(methyl-4-piperidinyl)-5-(2-methylthio4-pyrimidinyl)imidazole (2.7 g, 7.0 mmol) in glacial AcOH (150 mL). After stirring at ambient temperature for 72 h, the reaction mixture was neutralized by the portion-wise addition of concentrated aqueous NH4OH and extracted with CH2Cl2. The organic extract was washed with brine, dried (MgSO4) and concentrated. The residue was triturated with ethyl ether to afford the title compound as an off-white solid; yield 2.3 g (83%).

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-feb109733c514932b17dc91c5bea97c3
Source dataset
uspto-grants-2000_11
Patent number
US06150557

Reaction notes

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