Triethylamine → HCID 13423345, compound

HRID 1248579Notes

Reaction equation

HRID 1248579 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]2[O:8][C:9]3[C:14]([C:15](=[O:18])[C:16]=2[CH3:17])=[CH:13][CH:12]=[CH:11][C:10]=3[C:19](O)=[O:20])=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][NH2:42])[CH3:38]>O1CCCC1>[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][NH:42][C:19]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[O:8][C:7]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=1)=[C:16]([CH3:17])[C:15]2=[O:18])=[O:20])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 60993N,N-DiethylethylenediamineHCID 13288092HCID 13288092, compound

Product 1

HCID 13423345HCID 13423345, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 6.00 g of 4'-methoxy-3-methylflavone-8-carboxylic acid and 2.70 ml of triethylamine in 70 ml of anhydrous tetrahydrofuran was added a solution of 2.03 ml of ethyl chlorocarbonate in 10 ml of anhydrous tetrahydrofuran and the mixture was stirred for 1 hour under ice-cooling. To the reaction mixture was added a solution of 2.25 g of N,N-diethylethylenediamine in 10 ml of anhydrous tetrahydrofuran and the mixture was stirred for 1.5 hours under ice-cooling and further 16 hours at room temperature. The reaction mixture was treated by the same procedure as in Example 3(b), to give 3.55 g of pale yellow crystals, which were recrystallized from ethyl acetate as colorless needles, m.p. 125.5°-127° C. This compound was identical with the product obtained in Example 36(a) in NMR and IR spectra, and mixed m.p.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hours under ice-
  3. additionThe reaction mixture was treated by the same procedure as in Example 3(b)

Sources & evidence

ORD record
ord-d20c9c922c314ac5a0f3e89d5663d242
Source dataset
uspto-grants-1985_06
Patent number
US04525356

Reaction notes

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