Propiolic Acid → Propynoic acid-(4-prop-1-ynylphenyl)amide

HRID 734991Notes

Reaction equation

HRID 734991 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([OH:20])(=O)[C:17]#[CH:18].[C:21]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)#[C:22][CH3:23]>ClCCl>[C:21]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:16](=[O:20])[C:17]#[CH:18])=[CH:26][CH:25]=1)#[C:22][CH3:23]

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 450791534-(Prop-1-yn-1-yl)aniline

Product 1

HCID 86060737Propynoic acid-(4-prop-1-ynylphenyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.2 g (5.86 mmol) of DCC is added to a solution of 375 mg (5.35 mmol) of propynoic acid in 10 mL of dichloromethane at 0° C. and the mixture is stirred for 30 minutes. Then 0.7 g (5.35 mmol) of 4-prop-1-ynylphenylamine dissolved in dichloromethane is slowly added dropwise and the mixture is stirred for 2 hours again at 0° C. The reaction mixture is then filtered through CELITE® filter aid and the filtrate is evaporated down. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/ethanol (40:1)). Yield: 0.7 g (71.4% of theory); C12H9NO (M=183.21); calc.: molecular ion peak (M+H)+: 184; found: molecular ion peak (M+H)+: 184; Rf value: 0.65 (silica gel, dichloromethane/ethanol/acetic acid 20:1).

Workup

  1. additionis slowly added dropwise
  2. stirringthe mixture is stirred for 2 hours again at 0° C
  3. filtrationThe reaction mixture is then filtered through CELITE®
  4. filtrationfilter aid
  5. customthe filtrate is evaporated down
  6. customThe purification

Sources & evidence

ORD record
ord-fdd61de2abf54f519218407979ae1a1e
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…