3-(3-Chlorophenyl)-2-propynoic acid → 3-(3-chlorophenyl)-N-(2-(methyl(1,3,4-thiadiazol-2-yl)amino)ethyl)propiolamide

HRID 1677095Notes

Reaction equation

HRID 1677095 reaction equation
N=C=N.[CH3:4][N:5]([C:9]1[S:10][CH:11]=[N:12][N:13]=1)[CH2:6][CH2:7][NH2:8].[Cl:14][C:15]1[CH:16]=[C:17]([C:21]#[C:22][C:23](O)=[O:24])[CH:18]=[CH:19][CH:20]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]([C:21]#[C:22][C:23]([NH:8][CH2:7][CH2:6][N:5]([CH3:4])[C:9]2[S:10][CH:11]=[N:12][N:13]=2)=[O:24])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 238793-(3-Chlorophenyl)-2-propynoic acidHCID 160435CarbodiimideHCID 64158240N1-methyl-N1-(1,3,4-thiadiazol-2-yl)ethane-1,2-diamine

Product 1

HCID 598266903-(3-chlorophenyl)-N-(2-(methyl(1,3,4-thiadiazol-2-yl)amino)ethyl)propiolamideYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.25 g (≅4.0 mmol) PS carbodiimide was added to a solution of 317 mg (2.0 mmol) N1-methyl-N1-(1,3,4-thiadiazol-2-yl)ethane-1,2-diamine and 542 mg (3.0 mmol) 3-(3-chloro-phenyl)propiolic acid in DCM (20 ml) and the reaction solution was shaken for 16 h at RT. The resin was subsequently filtered off, washed with DCM and ethanol and the filtrate concentrated in a vacuum. CC (chloroform) was performed with the residue, whereby 165 mg (0.51 mmol, 26%) 3-(3-chlorophenyl)-N-(2-(methyl(1,3,4-thiadiazol-2-yl)amino)ethyl)propiolamide was obtained.

Workup

  1. filtrationThe resin was subsequently filtered off
  2. washwashed with DCM and ethanol
  3. concentrationthe filtrate concentrated in a vacuum

Sources & evidence

ORD record
ord-7e9f12e1eccd4cb482414b8d3c75ab38
Source dataset
uspto-grants-2011_08
Patent number
US08008304B2

Reaction notes

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