Thiourea → HCID 86666218, compound

HRID 705935Notes

Reaction equation

HRID 705935 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH:16]=[O:17])[C:11](OCC)=O)=[CH:5][CH:4]=1)#[N:2].[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C>[O:17]=[C:16]1[C:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:11][NH:21][C:19](=[S:20])[NH:18]1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86666189Ethyl 3-(4-cyanophenyl)-2-formylpropanoate

Product 1

HCID 86666218HCID 86666218, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 3-(4-cyanophenyl)-2-formylpropanoate (1.3 g, 5.62 mmol) in Ethanol (60 mL) was added thiourea (1.712 g, 22.49 mmol) under argon. The mixture was heated at 90° C. for 3 h. After removing the solvent, the residue was dissolved in water (80 mL), washed with ether twice. The aqueous solution was acidified to pH 4-5 with acetic acid, and the resulting precipitate was collected by filtration, washed with water until the wash waters were neutral to afford the title compound (0.95 g, 3.90 mmol, 69.5% yield). LCMS: rt=1.86 min, [M+H+]=224

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in water (80 mL)
  3. washwashed with ether twice
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water until the wash waters

Sources & evidence

ORD record
ord-211cfae848a74f40a9e2a5d31814d09f
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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