Bromine → 5-Bromo-3-(phenylthio)pyridin-2-amine

HRID 335124ノート

反応式

HRID 335124 の反応式
[N+:1]([C:4]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O.[Br:17]Br>[Zn].CC(O)=O>[Br:17][C:7]1[CH:8]=[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([NH2:1])=[N:5][CH:6]=1

参加物

5

反応物 2

HCID 24408BromineHCID 669950202-Nitro-3-(phenylthio)pyridine

生成物 1

HCID 459260645-Bromo-3-(phenylthio)pyridin-2-amine収率 92.21%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

mL 2-Nitro-3-(phenylthio)pyridine (16.3 g, 70.2 mmol) and AcOH (250 mL) were cooled in a water bath. Zinc (22.9 g, 351 mmol) was slowly added and stirred for 5 minutes. Filtered through celite and the cake washed with CH2Cl2. The CH2Cl2 was removed and to the solution was added bromine (3.6 mL, 70.2 mmol). After 10 minutes, the HOAc was removed and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (1.5 L SiO2 and 30% EtOAc in hexanes) to afford the title compound (18.2 g, 92.21% yield).

後処理

  1. filtrationFiltered through celite
  2. washthe cake washed with CH2Cl2
  3. customThe CH2Cl2 was removed and to the solution
  4. waitAfter 10 minutes
  5. customthe HOAc was removed
  6. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on silica gel (1.5 L SiO2 and 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-b9963ac8602f420c9212669806f6d897
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

反応ノート

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