Tetrahydrofuran → 2-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole

HRID 2094404ノート

反応式

HRID 2094404 の反応式
O[C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[N:18]1[CH:17]=[CH:16][C:15]([C:14]2[O:21][C:2]3[CH:7]=[CH:6][C:5]([S:8][C:9]([F:10])([F:11])[F:12])=[CH:4][C:3]=3[N:13]=2)=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate2 回HCID 66880242HCID 66880242、化合物

生成物 1

HCID 668807602-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole収率 26.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a mixture of 0.69 g of N-[2-hydroxy-5-(trifluoromethylthio)phenyl]isonicotinamide, 9 ml of tetrahydrofuran, and 0.63 g of triphenylphosphine, 1.05 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred for three hours. To the mixture, 0.21 g of triphenylphosphine and 0.35 g of 40% toluene solution of diethyl azodicarboxylate were added. The reaction mixture was stirred for further two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals were washed with methanol to give 0.17 g of 2-(pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole (hereinafter, referred to as “active compound 76”).

後処理

  1. additionwas added dropwise at room temperature
  2. stirringThe reaction mixture was stirred for further two hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe resultant crystals were washed with methanol

出典と根拠

ORDレコード
ord-ffe076cff0634084be329ba693cff88d
出典データセット
uspto-grants-2013_05
特許番号
US08445522B2

反応ノート

読み込み中…