Hydrochloric Acid → 5-Chloro-3-methyl-6-(pyrrol-1-yl)-benzofuran

HRID 637695Notes

Reaction equation

HRID 637695 reaction equation
Cl.[NH2:2][C:3]1[C:12]([Cl:13])=[CH:11][C:6]2[C:7]([CH3:10])=[CH:8][O:9][C:5]=2[CH:4]=1.CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1>O1CCOCC1>[Cl:13][C:12]1[C:3]([N:2]2[CH:16]=[CH:20][CH:19]=[CH:18]2)=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 202556476-Amino-5-chloro-3-methylbenzofuran

Product 1

HCID 202556465-Chloro-3-methyl-6-(pyrrol-1-yl)-benzofuran

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7 ml of 5N hydrochloric acid are added to a mixture of 9.1 g (50 mmole) of 6-amino-5-chloro-3-methylbenzofuran, 10 ml (78 mmole) of 2,5-dimethoxytetrahydrofuran and 200 ml of dioxane and the whole is stirred at room temperature for 16 hours. The whole is subsequently concentrated by evaporation in vacuo and the residue is chromatographed over silica gel with petroleum ether/methylene chloride. Crystallisation of the resulting product from petroleum ether yields 5-chloro-3-methyl-6-(pyrrol-1-yl)-benzofuran having a melting point of 49°-52°.

Workup

  1. concentrationThe whole is subsequently concentrated by evaporation in vacuo
  2. customthe residue is chromatographed over silica gel with petroleum ether/methylene chloride
  3. customCrystallisation of the resulting product from petroleum ether

Sources & evidence

ORD record
ord-e54f226f218f4830919c9ad19dad9aec
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…