Hydrochloric Acid → HCID 13576914, compound

HRID 544730Notes

Reaction equation

HRID 544730 reaction equation
[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:5]2[CH:6]([CH3:10])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1.Cl>O1CCOCC1>[CH3:10][CH:6]1[C:5]2[CH:11]=[C:12]([CH3:13])[C:2]([N:1]3[CH:16]=[CH:20][CH:19]=[CH:18]3)=[CH:3][C:4]=2[O:8][C:7]1=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 20458178HCID 20458178, compound

Product 1

HCID 13576914HCID 13576914, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.8 g of 6-amino-3,5-dimethylbenzofuran-2-(3H)-one are dissolved in 20 ml of dioxane and, while stirring at room temperature, 2 ml of 2,5-dimethoxy-tetrahydrofuran and 1.4 ml of 37% strength hydrochloric acid are added. After 30 minutes the aqueous phase is removed and the organic phase is concentrated to dryness by evaporation in vacuo. The residue is chromatographed over silica gel with methylene chloride. The resulting pale-yellow oil crystallises from butyl oxide. In this manner 3,5-dimethyl-6-(pyrrol-1-yl)-benzofuran-2(3H)-one having a melting point of 61°-63° C. is obtained.

Workup

  1. customAfter 30 minutes the aqueous phase is removed
  2. concentrationthe organic phase is concentrated to dryness by evaporation in vacuo
  3. customThe residue is chromatographed over silica gel with methylene chloride
  4. customThe resulting pale-yellow oil crystallises from butyl oxide

Sources & evidence

ORD record
ord-1845904e6aed47a8a58b21a6af89a87e
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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