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1-Chloro-3-(2-cyanoethylthio)propanone → 3-(2-(Diaminomethyleneamino)thiazol-4-yl)methylthio)propiononitrile

HRID 2165916
Notes
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Reaction equation

HRID 2165916 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][S:5][CH2:6][CH2:7][C:8]#[N:9].[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=[NH:13])[NH2:12]>CC(C)=O>[C:8]([CH2:7][CH2:6][S:5][CH2:4][C:3]1[N:17]=[C:15]([N:14]=[C:11]([NH2:13])[NH2:12])[S:16][CH:2]=1)#[N:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 541286781-Chloro-3-(2-cyanoethylthio)propanoneHCID 178513045HCID 178513045, compound

Product 1

HCID 50752593-(2-(Diaminomethyleneamino)thiazol-4-yl)methylthio)propiononitrileYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8.9 g of 1-chloro-3-(2-cyanoethylthio)propanone in 100 ml of acetone is added 6.3 g of amidinothiourea and the reaction mixture is stirred at 50° C. for 9 hours. Also, the reaction mixture is concentrated under reduced pressure, made basic with saturated sodium carbonate solution, and extracted with chloroformmethanol (10:1) solution (170 ml×2). The combined organic layer is dried over anhydrous magnesium sulfate, and is concentrated in vacuo to give a solid, which is crystallized from acetone-hexane to afford 10.2 g of the title compound, m.p.: 125°-128° C.

Workup

  1. concentrationAlso, the reaction mixture is concentrated under reduced pressure
  2. extractionextracted with chloroformmethanol (10:1) solution (170 ml×2)
  3. dry with materialThe combined organic layer is dried over anhydrous magnesium sulfate
  4. concentrationis concentrated in vacuo
  5. customto give a solid, which
  6. customis crystallized from acetone-hexane

Sources & evidence

ORD record
ord-abe8842aea0244f5a2511401f2431421
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04942243

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes