Benzothiazole → HCID 178468679、化合物

HRID 1440483ノート

反応式

HRID 1440483 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.S.[K].[S:18]1C2C=CC=CC=2N=C1>C(O)C.Cl>[CH2:14]([O:13][C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([SH:18])[S:3][C:4]=2[CH:10]=1)=[O:12])[CH3:15]

参加物

6

反応物 3

HCID 7222BenzothiazoleHCID 12067225Ethyl 2-bromo-6-benzothiazolecarboxylateHCID 86743134Potassium hydrogensulfide

生成物 1

HCID 178468679HCID 178468679、化合物

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

The crude 2-bromo-6-ethoxycarbonylbenzothiazole (1.90 g, 6.64 mmol) from Step 2 was suspended in absolute ethanol (35 mL) and treated with potassium hydrogen sulfide (0.96 g, 13.3 mmol). The mixture was placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 80° C. The benzothiazole starting material gradually went into solution. After heating for 30 minutes,the mixture was cooled in an ice bath, treated with IN hydrochloric acid (13.5 mL), and evaporated under vacuum. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL) and the aqueous phase extracted with more ethyl acetate (50 mL). The combined ethyl acetate solution was washed with brine (50 mL), dried over sodium sulfate, filtered and evaporated under vacuum to a yellow-tan solid (1.56 g). This material was triturated with diethyl ether and dried under vacuum to provide 6-ethoxycarbonyl-2-mercaptobenzothiazole (1.14 g) as a pale tan powder.

後処理

  1. temperatureAfter heating for 30 minutes
  2. temperaturethe mixture was cooled in an ice bath
  3. customevaporated under vacuum
  4. customThe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  5. extractionthe aqueous phase extracted with more ethyl acetate (50 mL)
  6. washThe combined ethyl acetate solution was washed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum to a yellow-tan solid (1.56 g)
  10. customThis material was triturated with diethyl ether
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-b5bfecd550fa46f298186d0f259d1567
出典データセット
uspto-grants-1996_03
特許番号
US05498777

反応ノート

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