2-Furancarbonyl chloride → HCID 14032527, compound

HRID 652144Notes

Reaction equation

HRID 652144 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([Cl:24])=[O:23]>C(Cl)(Cl)Cl>[ClH:24].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[N:9]1)=[O:23]

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 178480237HCID 178480237, compound

Product 1

HCID 14032527HCID 14032527, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole, 2.7 ml of 2-furoyl chloride (95% pure) and 60 ml of chloroform was refluxed for 3 hrs. The mixture was filtered. The filtrate was evaporated under reduced pressure, the residue was triturated and ethyl acetate and the solid was collected. The solid and filtrate were combined and recrystallized twice from ethanol to yield 3.3 g (51.5%) of product, mp 268°-270° C.

Workup

  1. temperaturewas refluxed for 3 hrs
  2. filtrationThe mixture was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was triturated
  5. customethyl acetate and the solid was collected
  6. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-7af0e8c0acff45bf95a6662210b5c377
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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