Potassium Carbonate → 2-(4,4-Difluorobut-3-enylthio)benzthiazole

HRID 2328

反応式

HRID 2328 の反応式
Br[CH2:2][CH2:3][CH:4]=[C:5]([F:7])[F:6].C(=O)([O-])[O-].[K+].[K+].[SH:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1>ClCCl>[F:6][C:5]([F:7])=[CH:4][CH2:3][CH2:2][S:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 27822404-Bromo-1,1-difluorobut-1-ene2 回HCID 178418395HCID 178418395、化合物

生成物 1

HCID 217129092-(4,4-Difluorobut-3-enylthio)benzthiazole収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
55 °C

実験手順

To the solution of 4-bromo-1,1-difluorobut-1-ene prepared in Example 6 was added potassium carbonate (10.76 g) and 2-mercaptobenzthiazole (9.18 g). The mixture was stirred at 55° C. for 6 hours and then at room temperature overnight. Gas-liquid chromatography of a sample of the reaction mixture showed that a small amount of 4-bromo-1,1-difluorobut-1-ene remained. More potassium carbonate (1.0 g) was added and the mixture heated for another two and a half hours at 55° C., when all of the bromo compound had been consumed. The mixture was cooled to room temperature and filtered. The residue was washed with acetone and the filtrate and washings combined and evaporated under reduced pressure to give the crude product (16.18 g). This was dissolved in dichloromethane. The solution was filtered and washed with dilute sodium hydroxide (2×25 ml) and with brine (2×25 ml), dried over magnesium sulphate, filtered, the filtrate evaporated to give 2-(4,4-difluorobut-3-enyl)thiobenzthiazole, having a gas chromatographic retention time identical with that of an authentic sample. The yield was 63% based on the quantity of 1,4-dibromo-1,1,2-trifluorobutane used in step (b) of Example 1. 2-(4,4-Difluorobut-3-enyl)thiobenzoxazole was prepared in the same way, but using 2-mercapto benzoxazole instead of 2-mercapto benzthiazole.

後処理

  1. customat room temperature
  2. customovernight
  3. temperaturethe mixture heated for another two and a half hours at 55° C.
  4. customwhen all of the bromo compound had been consumed
  5. temperatureThe mixture was cooled to room temperature
  6. filtrationfiltered
  7. washThe residue was washed with acetone
  8. customevaporated under reduced pressure
  9. customto give the crude product (16.18 g)
  10. filtrationThe solution was filtered
  11. washwashed with dilute sodium hydroxide (2×25 ml) and with brine (2×25 ml)
  12. dry with materialdried over magnesium sulphate
  13. filtrationfiltered
  14. customthe filtrate evaporated

出典と根拠

ORDレコード
ord-c607dee34d244a7e8f565c496317fb94
出典データセット
uspto-grants-1998_03
特許番号
US05728833

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