Carbon Disulfide → 5-(trifluoromethyl)-1,3-benzothiazole-2-thiol

HRID 9574

反応式

HRID 9574 の反応式
[H-].[Na+].C(OCCOCCO)C.Cl[C:13]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=1[NH2:15].[C:24](=[S:26])=[S:25]>>[SH:26][C:24]1[S:25][C:13]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=2[N:15]=1

参加物

5

反応物 4

HCID 6348Carbon DisulfideHCID 8146Diethylene Glycol Monoethyl EtherHCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 24758Sodium hydride

生成物 1

HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiol収率 44.1%

実験手順

To a mixture of sodium hydride (0.98 g, 40.91 mmol) and diethylene glycol monoethyl ether (25 mL) was added 2-chloro-5-(trifluoromethyl)aniline (5.00 g, 25.57 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at rt for 30 minutes, and then carbon disulfide (3.89 g, 51.13 mmol) was added. The reaction mixture was then heated at 140° C. for 6 hours. After cooling the solution to rt, the product was precipitated by addition of conc. HCl, collected by filtration, and recrystallized from isopropyl ether to afford 2-mercapto-5-(trifluoromethyl)benzothiazole (2.65 g, 44%). 1H NMR (400 MHz, DMSO-d6) δ 7.49 (s, 1H), 7.61 (d, 1H), 7.94 (d, 1H).

後処理

  1. temperatureThe reaction mixture was then heated at 140° C. for 6 hours
  2. temperatureAfter cooling the solution to rt
  3. customthe product was precipitated by addition of conc. HCl
  4. filtrationcollected by filtration
  5. customrecrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-661e57de66044a9898eced4c290b9652
出典データセット
uspto-grants-2006_08
特許番号
US07091228B2

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