Hydrochloric Acid → 2-[(2,5-Dichloropyrimidin-4-yl)amino]benzamide

HRID 2091928Notes

Reaction equation

HRID 2091928 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.Cl>CC(O)C>[Cl:11][C:12]1[N:17]=[C:16]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[C:15]([Cl:19])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6942AnthranilamideHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 579741762-[(2,5-Dichloropyrimidin-4-yl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-aminobenzamide (681 mg, 5.0 mmol), 2,4,5-trichloropyrimidine (2.75 g, 15 mmol, 3 equiv.) and concentrated HCl (aq) (1.72 mL, 20 mmol, 4 equiv.) in 2-propanol (100 mL) is heated at 60° C. for 12 h. The 2-propanol solvent is removed in vacuo. The resulting residue is neutralized to approximately pH=7 by adding 1 N NaOH (aq) followed by partition between EtOAc and water. Upon partition between EtOAc and water, a significant amount of precipitate is produced. This precipitate is collected by vacuum filtration and washed with small amounts of EtOAc and water, providing the product 2-(2,5-dichloropyrimidin-4-ylamino)benzamide; ESMS m/z 283.0 (M+H+).

Workup

  1. customThe 2-propanol solvent is removed in vacuo
  2. additionby adding 1 N NaOH (aq)
  3. customby partition between EtOAc and water
  4. customUpon partition between EtOAc and water
  5. customa significant amount of precipitate is produced
  6. filtrationThis precipitate is collected by vacuum filtration
  7. washwashed with small amounts of EtOAc and water

Sources & evidence

ORD record
ord-487c29f2b1664b09bdc4c549ddda7e0d
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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