Hydrochloric Acid → n-(3,5-Dichloropyrid-4-yl)-7-methoxy-2-methylbenzofuran-4-carboxamide

HRID 322032Notes

Reaction equation

HRID 322032 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11].[H][H].[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:26](O)=[O:27])=[C:20]2[C:24]=1[O:23][C:22]([CH3:25])=[CH:21]2.S(Cl)(Cl)=O.Cl>O1CCCC1.C1(C)C=CC=CC=1>[Cl:11][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]=1[NH:3][C:26]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[C:24]2[O:23][C:22]([CH3:25])=[CH:21][C:20]=12)=[O:27]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 220095237-Methoxy-2-methylbenzo[b]furan-4-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 22009540n-(3,5-Dichloropyrid-4-yl)-7-methoxy-2-methylbenzofuran-4-carboxamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of sodium hydride (80% strength) were added in small portions to a solution of 4.1 g of 4-amino3,5-dichloropyridine in 50 ml of tetrahydrofuran and the suspension was stirred for about 0.5 h until evolution of hydrogen had ended. In parallel to this, 4.1 g of 7-methoxy-2-methylbenzofuran-4-carboxylic acid was stirred at 80° C. for 3 h with 7.25 ml of thionyl chloride in 40 ml of toluene and the mixture was then evaporated in vacuo. About 20 ml of toluene were added to the residue and the solution was evaporated again in vacuo. The residue was then taken up in 50 ml of tetrahydrofuran and this solution was added dropwise at RT to the prepared suspension. After reaction was complete, the mixture was stirred into about 200 ml of ice water, treated with 30 ml of 2 N hydrochloric acid and extracted with ethyl acetate. This extract was dried over calcined sodium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate/petroleum spirit (b.p. 50-80° C.): m.p. 233° C.

Workup

  1. customthe mixture was then evaporated in vacuo
  2. additionAbout 20 ml of toluene were added to the residue
  3. customthe solution was evaporated again in vacuo
  4. additionthis solution was added dropwise at RT to the prepared suspension
  5. customAfter reaction
  6. extractionextracted with ethyl acetate
  7. customThis extract was dried
  8. customevaporated in vacuo
  9. customThe residue was crystallized from ethyl acetate/petroleum spirit (b.p. 50-80° C.)

Sources & evidence

ORD record
ord-bdb8822eff1542c9b8722de7ce53fa15
Source dataset
uspto-grants-2001_04
Patent number
US06211203B1

Reaction notes

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