Sodium Azide → HCID 22130676, compound

HRID 1416018Notes

Reaction equation

HRID 1416018 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH3:20])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[N:21]([CH2:2][C:3]1[N:4]([CH3:20])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 221306052-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole

Product 1

HCID 22130676HCID 22130676, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To dry dimethylformamide solution (70 ml)of 23.7 g of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol (28a)was added 5.30 g of sodium azide, and the mixture was stirred with heating at 80° C. for 16 hours. The reaction mixture was added to ice-water, and extracted with diethyl ether. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and 24.2 g of 2-azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (29a) was obtained (yield about 100%). mp 84-85° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4683f3c654b947f9b61de9fcdd72807c
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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