Thionyl Chloride → HCID 86613894, compound

HRID 598168Notes

Reaction equation

HRID 598168 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[N:7]=[CH:8][N:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[CH3:21])[C:10]=1[C:11](O)=[O:12]>CN(C=O)C>[ClH:3].[Br:5][C:6]1[N:7]=[CH:8][N:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[CH3:21])[C:10]=1[C:11]([Cl:3])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67266689HCID 67266689, compound

Product 1

HCID 86613894HCID 86613894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
75 °C

Procedure

To 8 mL of thionyl chloride was added 1.2 g (3.9 mmol) of 4-bromo-1-(2,4-dimethylphenyl)-1H-imidazole-5-carboxylic acid and 2 drops of DMF. The solution was heated to 75° C. for 4 h. The resulting slurry was cooled to room temperature and the white precipitate was collected by filtration. The precipitate was then slurried in ethyl acetate, collected by filtration and dried to give 0.81 g of the title compound as a white solid. The original filtrate was also concentrated and slurried in ethyl acetate to give an additional 0.21 g of the title compound. The overall yield of the title compound was 1.02 g (74%).

Workup

  1. temperatureThe resulting slurry was cooled to room temperature
  2. filtrationthe white precipitate was collected by filtration
  3. filtrationcollected by filtration
  4. customdried

Sources & evidence

ORD record
ord-45b327705a434480995beaf2b347dd51
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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