Hydrochloric Acid → 2-Chloro-4-(2,5-dichloroanilino)pyrimidine

HRID 347742

Reaction equation

HRID 347742 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:11]=1[NH2:12].Cl>C(O)CCC>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C:11]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:10]=2[Cl:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72622,5-DichloroanilineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 179811312-Chloro-4-(2,5-dichloroanilino)pyrimidineYield 20%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2,4-Dichloropyrimidine (50 g, 0.34 mol), 2,5-dichloroaniline (54.38 g, 0.34 mol) and concentrated hydrochloric acid (cat. amount) were dissolved in n-butanol (250 ml). The reaction mixture was stirred at room temperature for 12 hours after which the solid that had formed was collected by filtration. The organics were allowed to stand for 48 hours and the solid that formed was collected by filtration, washed with EtOAc and dried to give the title product as a white solid (18.65 g). NMR (300 MHz): 6.82 (d, 1H), 7.31 (dd, 1H), 7.58 (d, 1H), 7.82 (s, 1H), 8.19 (d, 1H), 9.82 (s, 1H); m/z: (ES+) 273.9 (MH+).

Workup

  1. customthat had formed
  2. filtrationwas collected by filtration
  3. waitto stand for 48 hours
  4. customthe solid that formed
  5. filtrationwas collected by filtration
  6. washwashed with EtOAc
  7. customdried

Sources & evidence

ORD record
ord-44c263d9e5d5409fb10eec7b770bee1f
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Linked notes

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