Triethylamine → HCID 13393817, compound

HRID 978783Notes

Reaction equation

HRID 978783 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].Cl.[CH2:21]([O:23][C:24](=[O:28])[CH2:25][NH:26][CH3:27])[CH3:22].C(N(CC)CC)C.[OH-].[K+]>N1C=CC=CC=1.O>[CH:18]([C:3]1[CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:5][C:6]2[C:11]([C:2]=1[N:26]([CH3:27])[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:28])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 13393783HCID 13393783, compound

Product 1

HCID 13393817HCID 13393817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
2 °C

Procedure

A solution of 1.0 g 4-chloro-3-formyl-flav-3-ene and 0.68 g sarcosin ethyl ester hydrochloride in 10 ml pyridine is cooled at 10°-15° C. One adds 0.97 g triethylamine and warms at 55° C. for 60 hours. After cooling to 2° C., 0.74 ml 50% potassium hydroxide solution is added. After 10 minutes, one adds 37 ml water. The mixture is extracted with dichloromethane, dried over magnesium sulfate and evaporated. The residue is purified by column chromatography on silica gel using dichloromethane as eluant. The solid is crystallized in dichloromethane. Pure 3-formyl-4-(N-methyl-N-ethoxycarbonylmethylamino)flav-3-ene is obtained as yellow crystals; m.p. 158°-159° C.

Workup

  1. waitAfter 10 minutes
  2. extractionThe mixture is extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel
  6. customThe solid is crystallized in dichloromethane

Sources & evidence

ORD record
ord-5caa1ae865ba4b5a9c3aa5c898ab97cc
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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