Triethylamine → HCID 2327631, compound

HRID 1602321Notes

Reaction equation

HRID 1602321 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 77070Veratroyl chloride

Product 1

HCID 2327631HCID 2327631, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 100 ml of methylene chloride, 21.3 g of 2-amino-4-ethoxycarbonyl-1,3-thiazole was suspended, followed by the addition of 24.8 g of 3,4-dimethoxybenzoyl chloride, 25.3 g of triethylamine and 0.15 g of 4-dimethylaminopyridine. The resulting mixture was refluxed for 2 hours. After the reaction mixture was allowed to cool down, methylene chloride was distilled off under reduced pressure. To the residue, 1000 ml of water was added. Crystals so precipitated were collected by filtration and then recrystallized from ethanol, whereby 30.3 g of the title compound was obtained. Yield: 73%.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. temperatureto cool down
  3. distillationmethylene chloride was distilled off under reduced pressure
  4. additionTo the residue, 1000 ml of water was added
  5. customCrystals so precipitated
  6. filtrationwere collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6b4915ea40e54809914a4e7b91b69a71
Source dataset
uspto-grants-1999_11
Patent number
US05981557

Reaction notes

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