Hydrochloric Acid → Tetomilast

HRID 2283519ノート

反応式

HRID 2283519 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[N:23]=[C:22]([C:24]([O:26]C)=[O:25])[CH:21]=[CH:20][CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[OH-].[Na+].C(O)C.Cl>O.C(OCC)(=O)C>[CH3:12][CH2:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([C:24]([OH:26])=[O:25])[N:23]=3)[N:17]=2)=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 10385338HCID 10385338、化合物

生成物 1

HCID 3025803Tetomilast

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

First, methyl 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]pyridin-2-carboxylate (49 g; 127 mmol) and 10% sodium hydroxide (100 ml) were added to ethanol (1.4 L), and the obtained mixture was then stirred for 4 hours under heating to reflux. A majority of solvent was eliminated from the obtained solution, and water and ethyl acetate were then added to the residue for separation. The water layer obtained as a result of the separation was changed to acidic by addition of 10% hydrochloric acid, followed by extraction with ethyl acetate. Thereafter, the extract was quickly washed with a saturated sodium chloride aqueous solution, and was then dried over an excessive amount of magnesium sulfate. The obtained mixture was recrystallized from ethyl acetate, so as to obtain an anhydrous tetomilast type B crystal.

後処理

  1. temperatureunder heating to reflux
  2. additionwere then added to the residue for separation
  3. customa result of the separation
  4. extractionfollowed by extraction with ethyl acetate
  5. washThereafter, the extract was quickly washed with a saturated sodium chloride aqueous solution
  6. dry with materialwas then dried over an excessive amount of magnesium sulfate
  7. customThe obtained mixture was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ba2f7ce34e5e49f491e627b65d97a2ab
出典データセット
uspto-grants-2015_09
特許番号
US09145404B2

反応ノート

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