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Water → 2-Methyl-6,7-dihydro-8H-indeno[5,4-d]thiazol-8-one

HRID 340672
ノート
印刷プレビュー

反応式

HRID 340672 の反応式
[NH2:1][C:2]1[C:10](I)=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:12])=[CH:4][CH:3]=1.[C:13](N)(=[S:15])[CH3:14].[O-2].[Ca+2].O>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][C:13]1[S:15][C:10]2[C:9]3[C:8](=[O:12])[CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][C:2]=2[N:1]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 2723949ThioacetamideHCID 6850728CalciumoxideHCID 577812296-amino-7-iodo-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 577812782-Methyl-6,7-dihydro-8H-indeno[5,4-d]thiazol-8-one収率 46%

試薬・触媒・溶媒 3

HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

6-Amino-7-iodoindan-1-one (1.00 g, 3.66 mmol), thioacetamide (413 mg, 5.49 mmol), 1,1′-bis(diphenylphosphino)ferrocene (383 mg, 1.46 mmol), calcium oxide (411 mg, 7.32 mmol) and tris(dibenzylideneacetone)dipalladium(0) (335 mg, 0.37 mmol) were dissolved in N,N-dimethylformamide (12 mL), and the mixture was stirred at 60° C. for 1 hr. After allowing to cool to room temperature, water was added to the reaction solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→65/35), and then purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60) to give the title compound (340 mg, yield 46%).

後処理

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→65/35)
  6. custompurified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60)

出典と根拠

ORDレコード
ord-7155badbed8b404691036620e8623e76
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895591B2

反応ノート

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