Triethylamine → HCID 178498980, compound

HRID 621422Notes

Reaction equation

HRID 621422 reaction equation
[NH2:1][C:2]([CH3:14])=[CH:3][C:4]([O:6][CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:5].[N+:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[CH:21]=[C:22]([C:27](OC)=[O:28])[C:23]([O:25][CH3:26])=[O:24])([O-:17])=[O:16].C(N(CC)CC)C>CC(O)C>[OH:28][C:27]1[NH:1][C:2]([CH3:14])=[C:3]([C:4]([O:6][CH2:7][CH2:8][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:5])[CH:21]([C:20]2[CH:31]=[CH:32][CH:33]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)[C:22]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 277557Dimethyl [(3-nitrophenyl)methylidene]propanedioateHCID 70042180HCID 70042180, compound

Product 1

HCID 178498980HCID 178498980, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-(2-thienyl)ethyl 3-amino-2-butenoate (1.8 g) and dimethyl 3-nitrobenzylidenemalonate (2.25 g) was dissolved in anhydrous 2-propanol (80 ml) and, after addition of triethylamine (27 ml), the mixture was refluxed for 21 hours. After the solvent was distilled off under reduced pressure, the residue was purified by thin-layer silica gel chromatography (developing solvent: chloroform/methanol=19/1; elution solvent: chloroform/acetone=2/1) so as to obtain 1.0 g (26%) of the desired compound.

Workup

  1. temperaturethe mixture was refluxed for 21 hours
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. customthe residue was purified by thin-layer silica gel chromatography (developing solvent: chloroform/methanol=19/1; elution solvent: chloroform/acetone=2/1) so as

Sources & evidence

ORD record
ord-4787a4725a8343178e31938c9a9a0c99
Source dataset
uspto-grants-1989_04
Patent number
US04824837

Reaction notes

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