Acetyl chloride → HCID 178475438, compound

HRID 437971Notes

Reaction equation

HRID 437971 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[O:8][C:7](=[O:11])[C:6](=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH3:13])[C:5]=1[OH:22])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31]>O1CCCC1>[C:30]([O:21][C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:12](=[C:6]2[C:5]([OH:22])=[C:4]([C:1](=[O:3])[CH3:2])[C:9](=[O:10])[O:8][C:7]2=[O:11])[CH3:13])=[CH:20][CH:19]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178467272HCID 178467272, compound

Product 1

HCID 178475438HCID 178475438, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.03 g. (0.01 m.) of 5-acetyl-4-hydroxy-3-[1-(p-hydroxyphenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, 1.0 g. (0.01 m.) of triethylamine in 150 ml. of tetrahydrofuran is added 0.78 g. (0.01 m.) of acetyl chloride. The resulting mixture is refluxed for two hours, cooled and filtered. The solid is recrystallized to give 3-[1-(p-acetoxyphenylamino)ethylidene]-5-acetyl-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 199°-201° C.

Workup

  1. temperatureThe resulting mixture is refluxed for two hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solid is recrystallized

Sources & evidence

ORD record
ord-40ae0d1bd6ff4a4f9e5d121e57a3e665
Source dataset
uspto-grants-1977_06
Patent number
US04032652

Reaction notes

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