Dimethylformamide → HCID 85443326, compound

HRID 127353Notes

Reaction equation

HRID 127353 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][C:5]=2[C:6](=[O:10])[C:7]=1[CH:8]=[O:9].CN(C)C=O.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[C:23]#[CH:24]>C(N(CC)CC)C>[CH2:15]([C:12]1[CH:13]=[CH:14][C:4]2[O:3][C:2]([NH:1][CH:24]=[CH:23][C:22]([O:26][CH2:27][CH3:28])=[O:25])=[C:7]([CH:8]=[O:9])[C:6](=[O:10])[C:5]=2[CH:11]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12182Ethyl propiolateHCID 126892482-Amino-6-ethyl-4-oxo-4H-1-benzopyran-3-carbaldehyde

Product 1

HCID 85443326HCID 85443326, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

A mixture consisting of 2.17 g of 2-amino-6-ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde, 25 ml of dimethylformamide, 5 g of ethyl propiolate and 0.1 ml of triethylamine was stirred at 90° C. for one hour and then the mixture was allowed to stand at room temperature. The resulting crystals were collected by filtration and recrystallized from acetone to obtain 1.65 g of ethyl 3-(6-ethyl-3-formyl-4-oxo-4H-1-benzopyran-2-yl)aminoacrylate as colorless needles melting at 201°-203° C.

Workup

  1. customto stand at room temperature
  2. filtrationThe resulting crystals were collected by filtration
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-f69dd84a16844e23baaffb3ddcb50323
Source dataset
uspto-grants-1981_03
Patent number
US04255576

Reaction notes

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