Acetone → Febuxostat

HRID 870885ノート

反応式

HRID 870885 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[S:15][C:16]([C:20]([O:22]CC)=[O:21])=[C:17]([CH3:19])[N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2].CC(C)=O.[OH-].[Na+].Cl>C(OCC)(=O)C.O>[CH3:19][C:17]1[N:18]=[C:14]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[C:3]([C:1]#[N:2])[CH:4]=2)[S:15][C:16]=1[C:20]([OH:22])=[O:21]

参加物

7

反応物 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98845495-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

生成物 1

HCID 134018Febuxostat収率 2.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (50.0 g), acetone (500 mL), water (200 mL), and sodium hydroxide (6.96 g) were placed into a round bottom flask and heated to reflux. The mixture was maintained under reflux until reaction completion. After the reaction was completed, the mass was cooled to about 25° C., water (500 mL) and ethyl acetate (500 mL) were added, and the pH was adjusted to about 1 to 2 with hydrochloric acid (10.3 mL). The organic layer was separated and the aqueous layer was extracted into ethyl acetate (250 mL). The ethyl acetate layer was washed with water (300 mL). The ethyl acetate layer was distilled completely under vacuum below 60° C. The residue was dried at about 60° C. under vacuum to a constant weight to yield 1.0 g of the title compound. Purity by HPLC: 98.9%.

後処理

  1. temperatureheated to reflux
  2. temperatureThe mixture was maintained
  3. temperatureunder reflux until reaction completion
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted into ethyl acetate (250 mL)
  6. washThe ethyl acetate layer was washed with water (300 mL)
  7. distillationThe ethyl acetate layer was distilled completely under vacuum below 60° C
  8. customThe residue was dried at about 60° C. under vacuum to a constant weight

出典と根拠

ORDレコード
ord-09a7848db7794e04a352488bcf3ae445
出典データセット
uspto-grants-2015_03
特許番号
US08969582B2

反応ノート

読み込み中…