4-Bromo-2-iodoaniline → Benzothiazole, 6-bromo-2-methyl-

HRID 2390664

反応式

HRID 2390664 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](I)[CH:3]=1.[CH3:10][C:11](N)=[S:12]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[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]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:11]([CH3:10])[S:12][C:4]=2[CH:3]=1

参加物

6

反応物 2

HCID 8239344-Bromo-2-iodoanilineHCID 2723949Thioacetamide

生成物 1

HCID 138448Benzothiazole, 6-bromo-2-methyl-収率 48.2%

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of 4-bromo-2-iodo-phenylamine (1.5 g, 5.0 mmol), thiacetamide (381 mg, 5.0), cupric oxide (280 mg, 3.5 mmol), dppf (56 mg, 0.10 mmol), Pd2(dba)3 (48 mg, 0.052 mmol) in DME was heated at 60° C. for 1 hour, cooled to room temperature, partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and concentrated. The concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride to give 550 mg (40% yield) of the desired product. MS (ESI(+)) m/e 227.8, 229.8 (M+H)+.

後処理

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride

出典と根拠

ORDレコード
ord-0cc6ea8707364b69bf6d9165d5632780
出典データセット
uspto-grants-2012_09
特許番号
US08273736B2

関連ノート

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