Carbon Disulfide → 4-Chlorobenzhydryl isothiocyanate

HRID 866856

反応式

HRID 866856 の反応式
[C:1](=[S:3])=S.C1(N=C=NC2CCCCC2)CCCCC1.[Cl:19][C:20]1[CH:33]=[CH:32][C:23]([CH:24]([NH2:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][CH:21]=1>CCOCC>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH:24]([N:31]=[C:1]=[S:3])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:32][CH:33]=1

参加物

5

反応物 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 409810(4-Chlorophenyl)(phenyl)methanamine

生成物 1

HCID 218286174-Chlorobenzhydryl isothiocyanate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-35 °C

実験手順

A mixture of 80 ml of carbon disulfide and 39.82 g (0.193 mole) of dicyclohexylcarbodimide in 100 ml of anhydrous ether, under dry N2, is cooled with stirring to -35° C. Then 42.23 g (0.194 mole) of p-chlorobenzhydrylamine in 500 ml of dry ether is added over about 5 min such that the temperature within the reaction vessel does not rise above -20° C. The temperature is allowed to rise slowly over 3 hrs. to ca.25° C and stirring is continued overnight. Dicyclohexylthiourea was removed by filtration and the filtrate is taken to dryness in vacuo. The cloudy oil is treated with 500 ml of pentane which dissolves the product and precipitates more insoluble impurities. Filtration through filter aid (diatomaceous earth) and solvent removal in vacuo gives p-chlorobenzhydryl isothiocyanate as an oil; IR (neat) 2140 cm-1.

後処理

  1. temperatureunder dry N2, is cooled
  2. customdoes not rise above -20° C
  3. stirring25° C and stirring
  4. waitis continued overnight
  5. customDicyclohexylthiourea was removed by filtration
  6. additionThe cloudy oil is treated with 500 ml of pentane which
  7. dissolutiondissolves the product
  8. customprecipitates more insoluble impurities
  9. filtrationFiltration
  10. filtrationthrough filter
  11. customaid (diatomaceous earth) and solvent removal in vacuo

出典と根拠

ORDレコード
ord-cb1438512cba4988b82dca88e1cc07b8
出典データセット
uspto-grants-1978_07
特許番号
US04101659

関連ノート

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