Isopropyl chloroformate → 1-p-Toluenesulfonyl-1-Carbisopropoxy-2-Carbamyl Hydrazine

HRID 46921

反応式

HRID 46921 の反応式
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[C:8]1([CH3:22])[CH:13]=[CH:12][C:11]([S:14]([NH:17][NH:18][C:19]([NH2:21])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[OH-].[K+]>O>[C:8]1([CH3:22])[CH:9]=[CH:10][C:11]([S:14]([N:17]([C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3])[NH:18][C:19](=[O:20])[NH2:21])(=[O:15])=[O:16])=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 7917Isopropyl chloroformateHCID 14797Potassium HydroxideHCID 82602p-Toluenesulfonylsemicarbazide

生成物 1

HCID 203859611-p-Toluenesulfonyl-1-Carbisopropoxy-2-Carbamyl Hydrazine

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
10 °C

実験手順

The reaction is conducted in a 2 liter reaction flask equipped with thermometer, mechanical stirrer, dropping funnel, and an ice-water bath. 400 ml. water is placed in the flask and cooled to 10° C. Then 73.4 g. (0.6 mole) of isopropyl chloroformate is added. The mixture is stirred at 10° C. as a filtered solution of 114.5 g. (0.5 moles) of p-toluenesulfonyl semicarbazide in a mixture of 36.5 g. (0.55 mole) of KOH in 400 ml. of water is dropped in over the period of an hour, keeping the temperature near 10° C. (A small amount (7.5 g.) of caustic insoluble solid is filtered from the p-toluenesultonyl semicarbazide salt solution). The reaction mixture in the flask is stirred for an additional hour as the temperature is allowed to rise to 25° C. (the cooling bath is removed). A heating mantle is applied and the stirred mixture is warmed to 45° C. The warm mixture is then filtered and the white crystalline product washed with water and dried overnight at 60° C. in a circulating hot air oven. Yield 145 g. (98.4%). m.p. 210°-212° C. A sample is treated with concentrated ammonium hydroxide, washed with water and dried. m.p.=211°-213° C.

後処理

  1. customThe reaction is conducted in a 2 liter reaction flask
  2. customequipped with thermometer, mechanical stirrer
  3. customnear 10° C.
  4. filtrationis filtered from the p-toluenesultonyl semicarbazide salt solution)
  5. stirringThe reaction mixture in the flask is stirred for an additional hour as the temperature
  6. customto rise to 25° C.
  7. customis removed)
  8. temperaturethe stirred mixture is warmed to 45° C
  9. filtrationThe warm mixture is then filtered
  10. washthe white crystalline product washed with water
  11. customdried overnight at 60° C. in a circulating hot air oven
  12. additionA sample is treated with concentrated ammonium hydroxide
  13. washwashed with water
  14. customdried

出典と根拠

ORDレコード
ord-d54ed9250267474ba28690bd9b62f4b9
出典データセット
uspto-grants-1979_11
特許番号
US04175200

関連ノート

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