Ammonium Chloride → HCID 178506249, compound

HRID 1687528Notes

Reaction equation

HRID 1687528 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[NH:6][CH:7]=1.[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([Cl:25])=[CH:20][N:19]=1.[Cl-].[NH4+]>CN(C)C=O>[Cl:17][C:18]1[N:23]=[C:22]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:5]2[NH:6][CH:7]=[C:3]([C:2]([F:1])([F:15])[F:16])[N:4]=2)[C:21]([Cl:25])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 178507485HCID 178507485, compound

Product 1

HCID 178506249HCID 178506249, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(4-Trifluoromethyl-1H-imidazol-2-yl)-phenylamine (0.200 g, 0.880 mmol) and 2,4,5-Trichloro-pyrimidine (0.161 g, 0.880 mmol) were dissolved in N,N-Dimethylformamide (5.0 mL) and the reaction was heated at 50° C. and was allowed to stir overnight. The reaction mixture was poured over saturated ammonium chloride, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 220 mg (67%) of the desired product.

Workup

  1. extractionorganics were extracted with ethyl acetate/dichloromethane
  2. dry with materialCombined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-156ebec7e3e542fcaff2a7788972132b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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