Potassium Carbonate → 5-(Pyridin-2-ylsulfanyl)-thiazol-2-ylamine

HRID 416251ノート

反応式

HRID 416251 の反応式
Br.[NH2:2][C:3]1[S:4][C:5](Br)=[CH:6][N:7]=1.[SH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:9][C:5]1[S:4][C:3]([NH2:2])=[N:7][CH:6]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 178418616HCID 178418616、化合物

生成物 1

HCID 157291575-(Pyridin-2-ylsulfanyl)-thiazol-2-ylamine収率 73.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-amino-5-bromothiazole hydrobromide (1.00 g, 3.85 mmol) in DMF (8 mL) was added 2-mercaptopyridine (428 mg, 3.85 mmol) followed by addition of powdered K2CO3 (1.81 g, 15.09 mmol). The mixture was stirred at 80° C. for 1 h and at rt for 16 h. The solvent was removed in vacuo at 80° C. and the compound was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc and the organic phase was extracted with HCl 1N. The acidic extract was neutralized with saturated NaHCO3 and the precipitate was extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound 169 (589 mg, 73% yield). 1H NMR: (Acetone-d6) δ(ppm): 8.36 (s, 1H), 7.66 (s, 1H), 7.20 (s, 1H), 7.12-7.05 (m, 2H), 6.84 (s, 2H). m/z: 210.1 (MH+).

後処理

  1. customThe solvent was removed in vacuo at 80° C.
  2. customthe compound was partitioned between H2O and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. extractionthe organic phase was extracted with HCl 1N
  5. extractionThe acidic extract
  6. extractionthe precipitate was extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c96fd53be5a949d58f2c224b04e5f97e
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

反応ノート

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