4-Chlorobenzoyl chloride → HCID 14032551, compound

HRID 652155Notes

Reaction equation

HRID 652155 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>CCOCC>[ClH:18].[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=3)[C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[N:7]2)=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 178480245HCID 178480245, compound

Product 1

HCID 14032551HCID 14032551, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.0 g of 6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole and 5 ml of 4-chlorobenzoyl chloride was heated at 100° C. in a steam bath for 2 hrs. After cooling, ether was added and the solid was collected. The solid was combined with a 2.5 g sample from another experiment and recrystallized twice from ethanol-ether to yield 4.7 g (56%, calculated on the combination of both experiments) of product, mp 258°-260° C.

Workup

  1. temperatureAfter cooling
  2. customthe solid was collected
  3. customrecrystallized twice from ethanol-ether
  4. customto yield 4.7 g (56%

Sources & evidence

ORD record
ord-152d80c8d03f4cc08b76e437902d9589
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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