3-(Phenylthio)-2-propenoic acid → HCID 68488496、化合物

HRID 1882338ノート

反応式

HRID 1882338 の反応式
[C:1]1([S:7][CH:8]=[CH:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[S:18][C:17]([S:19][CH3:20])=[N:16][CH:15]=1>C(#N)C.C(N(CC)CC)C>[CH3:20][S:19][C:17]1[S:18][C:14]([NH:13][C:10](=[O:12])[CH:9]=[CH:8][S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][N:16]=1

参加物

5

反応物 2

HCID 2757063-(Phenylthio)-2-propenoic acidHCID 132489052-(Methylsulfanyl)-1,3-thiazol-5-amine

生成物 1

HCID 68488496HCID 68488496、化合物収率 30.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To a solution of 3-(phenylthio)acrylic acid (3.69 g) in acetonitrile (50 mL) were added a solution of 5-amino-2-(methylthio)thiazole (3.00 g) in acetonitrile (10 mL) and triethylamine (2.80 mL) under ice-cooling. The mixture was stirred at the same temperature for 2 hours and then at room temperature for 3 hours, and then concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (50 mL), which was extracted with ethyl acetate (100 mL) twice. The organic layers were combined, washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain N-[2-(methylthio)thiazol-5-yl]-3-(phenylthio)acrylamide (1.90 g) as a dark yellow crystal.

後処理

  1. temperaturecooling
  2. waitat room temperature for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added 1N hydrochloric acid (50 mL), which
  5. extractionwas extracted with ethyl acetate (100 mL) twice
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9eecd080a22147d9806460c5a3f6c1f6
出典データセット
uspto-grants-2012_11
特許番号
US08318981B2

反応ノート

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