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

HRID 2091928ノート

反応式

HRID 2091928 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-487c29f2b1664b09bdc4c549ddda7e0d
出典データセット
uspto-grants-2013_05
特許番号
US08440681B2

反応ノート

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