Acetonitrile → 4-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

HRID 1834801ノート

反応式

HRID 1834801 の反応式
[S-:1][C:2]#[N:3].[K+].C(#N)C.Cl[C:9]([O:11][CH3:12])=[O:10].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH3:22])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>O>[CH2:21]([S:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:2]([NH:3][C:9]([O:11][CH3:12])=[O:10])=[S:1])=[C:15]([N+:23]([O-:25])=[O:24])[CH:16]=1)[CH3:22]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 6586Methyl chloroformateHCID 516872Potassium thiocyanateHCID 203720451-Amino-4-ethylthio-2-nitrobenzene

生成物 1

HCID 203720534-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene収率 39.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
10 °C

実験手順

A mixture of dry potassium thiocyanate (25.65 g) and acetonitrile (320 ml) was cooled to 10° C and treated during 5 minutes with methyl chloroformate (25.0 g). The mixture was stirred at room temperature for 2 hours. 1-Amino-4-ethylthio-2-nitrobenzene (22.45 g) was then added to the mixture at 10°-15° C. The suspension was stirred for 3 hours at room temperature and allowed to stand overnight. It was then poured into water (1.6 liters) and the solid which precipitated was filtered off, washed with water and recrystallised from a mixture of methanol and ethanol, to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene (14.0 g), m.p. 152° C.

後処理

  1. stirringThe suspension was stirred for 3 hours at room temperature
  2. waitto stand overnight
  3. customthe solid which precipitated
  4. filtrationwas filtered off
  5. washwashed with water
  6. customrecrystallised from a mixture of methanol and ethanol

出典と根拠

ORDレコード
ord-86aa24f01f074f9db913d9eeeda5f33a
出典データセット
uspto-grants-1978_01
特許番号
US04071528

反応ノート

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