3,4-Dichloroaniline → HCID 21923095, compound

HRID 1965941Notes

Reaction equation

HRID 1965941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl[C:11]1[N:16]=[C:15]([Cl:17])[C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]2[N:16]=[C:15]([Cl:17])[C:14]([C:18]([F:20])([F:21])[F:19])=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 11430Potassium CarbonateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 21923095HCID 21923095, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.86 g of 3,4-dichloroaniline dissolved in 10 ml of dioxane are added to 6.51 g of 2,4-dichloro-5-trifluoromethyl-pyrimidine in 40 ml of dioxane at ambient temperature. Then 6 ml of 5 M potassium carbonate solution are added and the mixture is stirred for three days at ambient temperature. It is then filtered through Alox B (20 ml) and washed with dioxane. The filtrate is concentrated by evaporation, the residue dissolved in 50 ml methylene chloride and this solution is cooled in a bath of dry ice and acetone. The precipitate is suction filtered and the filtrate is cooled again. After suction filtering again the precipitates are combined and the filtrate is concentrated by evaporation. The residue is separated by chromatography through an RP18 column (gradient: acetonitrile: H2O=20:80 to 80:20).

Workup

  1. filtrationIt is then filtered through Alox B (20 ml)
  2. washwashed with dioxane
  3. concentrationThe filtrate is concentrated by evaporation
  4. dissolutionthe residue dissolved in 50 ml methylene chloride
  5. temperaturethis solution is cooled in a bath of dry ice and acetone
  6. filtrationfiltered
  7. temperaturethe filtrate is cooled again
  8. filtrationAfter suction filtering again the precipitates
  9. concentrationthe filtrate is concentrated by evaporation
  10. customThe residue is separated by chromatography through an RP18 column (gradient: acetonitrile: H2O=20:80 to 80:20)

Sources & evidence

ORD record
ord-59b9740d392b4b75a61d33711ed6c912
Source dataset
uspto-grants-2013_04
Patent number
US08420630B2

Reaction notes

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