3,5-Dichlorobenzoyl chloride → HCID 22319552, compound

HRID 497636Notes

Reaction equation

HRID 497636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](Cl)=[O:6].[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([NH2:22])=[N:18][NH:19]2)=[CH:15][CH:14]=1>N1C=CC=CC=1>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([NH:22][C:5](=[O:6])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:10]=[C:9]([Cl:11])[CH:8]=3)=[N:18][NH:19]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 761913,5-Dichlorobenzoyl chlorideHCID 856286-chloro-1H-indazol-3-amine

Product 1

HCID 22319552HCID 22319552, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

0.83 cm3 of 3,5-dichlorobenzoyl chloride is added to 1 g of 6-chloro-1H-indazole-3-amine in 15 cm3 of pyridine, after cooling in an ice bath to about 3° C., and the mixture is then stirred for 10 minutes at this temperature and is allowed to return to room temperature over 18 hours. The reaction medium is then concentrated to dryness under reduced pressure (2 kPa; 50° C.) and the residue is taken up in 25 cm3 of ethyl acetate and 25 cm3 of water. The precipitate formed is filtered off and, after drying (90 Pa; 50° C.), 700 mg of N-[6-chloro-1H-indazol-3-yl]-3,5-dichlorobenzamide are obtained in the form of a white solid melting at about 240° C.

Workup

  1. waitto return to room temperature over 18 hours
  2. concentrationThe reaction medium is then concentrated to dryness under reduced pressure (2 kPa; 50° C.)
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. dry with materialafter drying (90 Pa; 50° C.), 700 mg of N-[6-chloro-1H-indazol-3-yl]-3,5-dichlorobenzamide

Sources & evidence

ORD record
ord-1cbcc5d097b24e0896f75306cb5a602b
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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