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

HRID 492713ノート

反応式

HRID 492713 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8af9d4ffcef348eeb558b025571d161c
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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