Chloroform → N-(2-{[(4-Bromo-1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)-N'-methylthiourea

HRID 847883

反応式

HRID 847883 の反応式
Br.[Br:2][C:3]1[C:4]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[N:5][S:6][CH:7]=1.[OH-].[Na+].C(Cl)(Cl)Cl.[CH3:19][N:20]=[C:21]=[S:22]>C(O)C>[CH3:19][NH:20][C:21]([NH:12][CH2:11][CH2:10][S:9][CH2:8][C:4]1[C:3]([Br:2])=[CH:7][S:6][N:5]=1)=[S:22]

参加物

6

反応物 4

HCID 6212ChloroformHCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 205500984-Bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide

生成物 1

HCID 12923381N-(2-{[(4-Bromo-1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)-N'-methylthiourea収率 108.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The reaction of 4-bromo-3-(bromomethyl)isothiazole (8.5 g.) with cysteamine (from cysteamine hydrochloride (3.76 g.)) was performed under conditions similar to those described in Example 122. From the reaction there was obtained 4-bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide, which, following recrystallisation from ethanol-ether and acetonitrile, gave needles (4.05 g.), m.p. 111°-112°. The amine base (2.73 g.) was isolated by basification with sodium hydroxide and extraction with chloroform and then dissolved in ethanol and treated with methyl isothiocyanate (0.78 g.). The solution was heated under reflux for 30 minutes, concentrated and the residue triturated with ether to yield the crystalline thiourea (2.9 g.) m.p. 60°-61°. Recrystallisation from isopropyl acetate gave N-methyl-N'-[2-((4-bromo-3-isothiazolyl)-methylthio)ethyl]thiourea (2.3 g.) as needles, m.p. 62°-63°.

後処理

  1. customrecrystallisation from ethanol-ether and acetonitrile
  2. customgave needles (4.05 g.), m.p. 111°-112°
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 30 minutes
  5. concentrationconcentrated
  6. customthe residue triturated with ether

出典と根拠

ORDレコード
ord-71211b78207047ca835a9c49287626fc
出典データセット
uspto-grants-1981_10
特許番号
US04293697

関連ノート

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