Phenylacetyl chloride → 2-Amino-4-{3-methoxy-4-[3-(2-phenylacetyl)thioureido]phenoxy}pyridine

HRID 492713Notes

Reaction equation

HRID 492713 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:11][C:12]#[N:13].[K+].[NH2:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([O:30][CH3:31])[CH:24]=2)[CH:19]=[CH:18][N:17]=1>C(#N)C>[NH2:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:12]([NH:13][C:8](=[O:9])[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[S:11])=[C:25]([O:30][CH3:31])[CH:24]=2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 516872Potassium thiocyanateHCID 231532722-Amino-4-(4-amino-3-methoxyphenoxy)pyridine

Product 1

HCID 576777282-Amino-4-{3-methoxy-4-[3-(2-phenylacetyl)thioureido]phenoxy}pyridineYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Phenylacetyl chloride (0.198 ml) was dissolved in acetonitrile (10 ml) under a nitrogen atmosphere, and then potassium thiocyanate (292 mg) was added at 60° C., followed by stirring at the same temperature for 3.5 hrs. The reaction mixture was cooled down to room temperature, and then 2-amino-4-(4-amino-3-methoxyphenoxy)pyridine (231.3 mg) was added thereto, followed by further stirring for 2 hrs. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=9:1) to provide the titled compound (158 mg, 39%) as pale brown powder.

Workup

  1. stirringby further stirring for 2 hrs
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with water and brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-8af9d4ffcef348eeb558b025571d161c
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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