海萝胶 → 2-氯-4,6-二氟苯并噻唑

HRID 9567

反应方程式

HRID 9567 反应方程式
N(OCCC(C)C)=O.[F:9][C:10]1[C:15]2[N:16]=[C:17](N)[S:18][C:14]=2[CH:13]=[C:12]([F:20])[CH:11]=1.[ClH:21]>C(#N)C.[Cu](Cl)Cl>[Cl:21][C:17]1[S:18][C:14]2[CH:13]=[C:12]([F:20])[CH:11]=[C:10]([F:9])[C:15]=2[N:16]=1

参与物

6

反应物 3

HCID 313海萝胶HCID 8053亚硝酸异戊酯HCID 7374064,6-二氟-1,3-苯并噻唑-2-胺

产物 1

HCID 20498832-氯-4,6-二氟苯并噻唑收率 99%

试剂、催化剂与溶剂 2

HCID 24014氯化铜催化剂HCID 6342乙腈溶剂

实验过程

To a solution containing copper chloride (II) (0.87 g, 6.45 mmol) and tri(ethylene glycol) dimethyl ether (3 mL) in acetonitrile (50 mL) was added isoamyl nitrite (0.94 g, 8.06 mmol), and the reaction mixture was stirred at rt for 30 minutes. To this suspension was added dropwise a solution of 4,6-difluoro-1,3-benzothiazol-2-amine (1.0 g, 5.37 mmol) in tri(ethylene glycol) dimethyl ether (5 mL). The reaction mixture was stirred at rt for 10 minutes, and then heated at 50° C. for 2.5 h. The reaction mixture was cooled to rt, and then poured cautiously into cold aqueous 6 M HCl (200 mL). The solution was extracted with EtOAc. The organic layer was washed with HCl (1.0 M), water and brine, filtered and concentrated down to afford 2-chloro-4,6-difluoro-1,3-benzothiazole (1.1 g, 99%). 1H NMR (400 MHz, DMSO-d6) 7.05 (m, 1H), 7.36 (m, 1H).

后处理

  1. stirringThe reaction mixture was stirred at rt for 10 minutes
  2. temperatureheated at 50° C. for 2.5 h
  3. temperatureThe reaction mixture was cooled to rt
  4. extractionThe solution was extracted with EtOAc
  5. washThe organic layer was washed with HCl (1.0 M), water and brine
  6. filtrationfiltered
  7. concentrationconcentrated down

来源与证据

ORD记录
ord-b1d3138809e7413ab40947cf032e2724
来源数据集
uspto-grants-2006_08
专利号
US07091228B2

关联笔记

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