Hydrochloric Acid → HCID 20255631, compound

HRID 637690Notes

Reaction equation

HRID 637690 reaction equation
Cl.[NH2:2][C:3]1[C:12]([CH3:13])=[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>[CH3:10][C:7]1[C:6]2[CH:11]=[C:12]([CH3:13])[C:3]([N:2]3[CH:16]=[CH:20][CH:19]=[CH:18]3)=[CH:4][C:5]=2[O:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 20255642HCID 20255642, compound

Product 1

HCID 20255631HCID 20255631, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5 ml of 6N hydrochloric acid are added to a mixture of 7.5 g (46.5 mmole) of 6-amino-3,5-dimethylbenzofuran, 7.5 ml (58 mmole) of 2,5-dimethoxytetrahyrofuran and 150 ml of dioxane and the whole is boiled under reflux for 40 minutes. The whole is concentrated by evaporation in vacuo and the residue is taken up in methylene chloride and washed three times with water. The crude product obtained after drying and concentration by evaporation of the organic phase is chromatographed over silica gel with petroleum ether/ether. Subsequent distillation of the pure fractions in a bulb tube (120°/4.10-2 torr) yields 3,5-dimethyl-6-(pyrrol-1-yl)-benzofuran having a melting point of 43°-45°.

Workup

  1. temperatureunder reflux for 40 minutes
  2. concentrationThe whole is concentrated by evaporation in vacuo
  3. washwashed three times with water
  4. customThe crude product obtained
  5. customafter drying
  6. concentrationconcentration
  7. customby evaporation of the organic phase
  8. customis chromatographed over silica gel with petroleum ether/ether
  9. distillationSubsequent distillation of the pure fractions in a bulb tube (120°/4.10-2 torr)

Sources & evidence

ORD record
ord-ebbba19427ec40b78acb5a5c72108244
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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