Triethylamine → N-methyl-N-(3,4-dimethoxycinnamyl)-3,4,5-trimethoxyphenylpropiolamide

HRID 1282926Notes

Reaction equation

HRID 1282926 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.[CH3:31][NH:32][CH2:33][CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1>O1CCCC1.C(OCC)C.C(Cl)Cl>[CH3:31][N:32]([CH2:33][CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1)[C:15](=[O:17])[C:14]#[C:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 125218533-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acidHCID 53660943N-methyl-3,4-dimethoxycinnamylamine

Product 1

HCID 53953266N-methyl-N-(3,4-dimethoxycinnamyl)-3,4,5-trimethoxyphenylpropiolamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent3×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 11.6 g of 3,4,5-trimethoxyphenylpropiolic acid in 60 ml of tetrahydrofuran, 6.0 g of triethylamine are added while stirring, followed by 60 ml of diethyl ether. The mixture is cooled with ice and to the resulting suspension the solution of 5.35 g of ethyl chloroformate in 30 ml of diethyl ether is added dropwise. The mixture is stirred for 15 minutes at 0°-5°, whereupon the solution of 9.7 g of N-methyl-3,4-dimethoxycinnamylamine in 30 ml of diethyl ether is added dropwise, followed by 50 ml of methylene chloride. The mixture is stirred for 30 minutes at room temperature and washed with N hydrochloric acid, 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated under reduced pressure, to yield the N-methyl-N-(3,4-dimethoxycinnamyl)-3,4,5-trimethoxyphenylpropiolamide.

Workup

  1. additionis added dropwise
  2. additionis added dropwise
  3. stirringThe mixture is stirred for 30 minutes at room temperature
  4. washwashed with N hydrochloric acid, 2N aqueous sodium hydroxide and saturated aqueous sodium chloride
  5. customdried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-39d11d68f1c04fefabd7da7358481ff9
Source dataset
uspto-grants-1976_08
Patent number
US03973030

Reaction notes

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