4-Cyanothiazole → Thiabendazole

HRID 1033530

反応式

HRID 1033530 の反応式
[C:1]([C:3]1[N:4]=[CH:5][S:6][CH:7]=1)#[N:2].Cl.[C:9]1(N)[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15]>>[CH:13]1[CH:14]=[CH:9][C:10]2[N:15]=[C:1]([C:3]3[N:4]=[CH:5][S:6][CH:7]=3)[NH:2][C:11]=2[CH:12]=1

参加物

3

反応物 2

HCID 150694-CyanothiazoleHCID 5743464Benzene-o-diamine monohydrochloride

生成物 1

HCID 5430Thiabendazole収率 75.5%

反応条件

温度
201 °C

実験手順

The mixture was heated and when the pot temperature reached 164° C., distillation commenced. The temperature gradually increased to 201° C. and a total of 44 ml of water plus ethylene glycol distillate were removed. The mixture was allowed to cool to 100° C. before 27.5 g (0.25 moles) of 4-cyanothiazole were added to the solution containing o-phenylenediamine monohydrochloride. The reaction mixture was heated to 125° C. and held within a temperature range of 125°-130° C. for a period of 5 hours. Thiabendazole formed as a precipitte during the 5 hours of heating. The reaction was monitored by gas chromatography and determined to be complete when the peaks corresponding to o-phenylenediamine and 4-cyanothiazole were negligible. Next, the reaction mass was cooled to 50° C. and filtered to collect the precipitate using a Buchner funnel and #4 Whatman filter paper. The wet cake was washed with 1.5 L of deionized water. The washed precipitate was dried overnight in a vacuum oven under 15-20" Hg and at a temperature of 90° C. The weight of dry thiabendazole crystals was 38.0 g, which corresponds to a yield of 75.5%. The purity was determined to be 99.67% (based on area %) using HPLC analysis.

後処理

  1. temperatureThe mixture was heated
  2. customreached 164° C.
  3. distillationdistillation
  4. customa total of 44 ml of water plus ethylene glycol distillate were removed
  5. additionwere added to the solution
  6. temperatureThe reaction mixture was heated to 125° C.

出典と根拠

ORDレコード
ord-ec6ddd42289542fcae7ecc188b583293
出典データセット
uspto-grants-1994_05
特許番号
US05310923

関連ノート

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