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Triethylamine → 2-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-3-methoxythiophene-4-carboxamide

HRID 355736
ノート
印刷プレビュー

反応式

HRID 355736 の反応式
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:9]([OH:11])=O)[C:6]=1[O:7][CH3:8].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1>S(Cl)(Cl)=O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:9]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[C:22]([N:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)[CH:23]=2)=[O:11])[C:6]=1[O:7][CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27783935-Bromo-4-methoxythiophene-3-carboxylic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

生成物 1

HCID 189406682-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-3-methoxythiophene-4-carboxamide

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

2-Bromo-3-methoxythiophene-4-carboxylic acid (0.429 g; 1.81 mmol) was heated at reflux in thionyl chloride (8 ml) for 1 hour, cooled, evaporated in vacuo and the residue azeotroped with toluene. The orange residue was redissolved in CH2Cl2 (5 ml) and treated with dry triethylamine (0.25 ml;1.81 mmol) and 4-methoxy-3-(4-methyl-1-piperazinyl)benzenamine (0.4 g; 1.8mmol). The solution was stirred under Ar (18 hours), evaporated in vacuo and partitioned satd. K2CO3 (aq)/EtOAc. The organic phases were combined, dried over Na2SO4, filtered and the filtrate evaporated in vacuo to a brown gum. The gum was purified by flash silica-gel chromatography and eluted with 2%MeOH/CHCl3 to yield the title compound as white powder after trituration with Et2O (0.43 g;54%), mp=120-122° C.

後処理

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customthe residue azeotroped with toluene
  4. dissolutionThe orange residue was redissolved in CH2Cl2 (5 ml)
  5. customevaporated in vacuo
  6. custompartitioned
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo to a brown gum
  10. customThe gum was purified by flash silica-gel chromatography
  11. washeluted with 2%MeOH/CHCl3

出典と根拠

ORDレコード
ord-b376cf0f127e42d2ae4b06f7399101aa
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834471

反応ノート

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