Sodium Azide → 4-[3-azidomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine

HRID 1862470Notes

Reaction equation

HRID 1862470 reaction equation
Cl.Cl[CH2:3][C:4]1[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:7]([S:16][C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)[N:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C)C=O>[N:28]([CH2:3][C:4]1[C:8]([CH2:9][C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)=[C:7]([S:16][C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)[N:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 693533844-[3-chloromethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine hydrochloride

Product 1

HCID 867588894-[3-azidomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridineYield 106.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 120 mg of 4-[3-chloromethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine hydrochloride in 1 ml of anhydrous dimethylformamide stirred at room temperature was added 85 mg of sodium azide. The mixture was stirred for 1 h. The mixture was partitioned between diethyl ether and water then extracted three times. The combined extracts were reduced under reduced pressure to give 120 mg of 4-[3-azidomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine as a yellow oil which was used without any further purification. Mass spectrum (ESI) 433 [M+H]+.

Workup

  1. customThe mixture was partitioned between diethyl ether and water
  2. extractionthen extracted three times

Sources & evidence

ORD record
ord-2a751e8190c24792926f53898040f713
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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