Water → HCID 57493916、化合物

HRID 508351

反応式

HRID 508351 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[CH3:12][C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH3:17].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.O>C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([N:9]3[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]3[CH3:12])[S:8][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 80352,5-HexanedioneHCID 851492-Benzothiazolamine, 6-bromo-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 57493916HCID 57493916、化合物収率 84%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A solution 6-bromobenzo[d]thiazol-2-amine (5.75 g, 25.1 mmol), hexane-2,5-dione (2.95 mL, 25.1 mmol), and PPTS (0.95 g, 3.76 mmol) in benzene (100 ml) was refluxed for 16 h while water was removed with a Dean-Stark trap. The cooled mixture was poured into EtOAc (100 mL) and extracted with saturated aq. NaHCO3 (2×100 mL) and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 9:1 EtOAc:hexanes as the eluent to give the title compound as an orange oil (6.46 g, 84%).

後処理

  1. customwas removed with a Dean-Stark trap
  2. additionThe cooled mixture was poured into EtOAc (100 mL)
  3. extractionextracted with saturated aq. NaHCO3 (2×100 mL) and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using 9:1 EtOAc

出典と根拠

ORDレコード
ord-820f38f64ed24e64920365a25f92ae34
出典データセット
uspto-grants-2015_08
特許番号
US09095590B2

関連ノート

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