Triethylamine → HCID 22473796、化合物

HRID 2183662ノート

反応式

HRID 2183662 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:14]2[S:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1.Cl.[CH3:22][NH:23][O:24][CH3:25].C(N(CC)CC)C>ClCCl.CN(C)C=O.O>[CH3:25][O:24][N:23]([CH3:22])[C:18]([C:16]1[S:15][C:14]2[C:9]([O:8][CH3:7])=[CH:10][CH:11]=[CH:12][C:13]=2[CH:17]=1)=[O:20]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 8217517-Methoxybenzo[b]thiophene-2-carboxylic acid

生成物 1

HCID 22473796HCID 22473796、化合物収率 65.4%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Oxalyl chloride (1 ml) was added dropwise under nitrogen at 0° C. to a stirred suspension of 7-methoxybenzo[b]thiophene-2-carboxylic acid (1.9 g) in dichloromethane (25 ml), then dimethylformamide (2 drops) was added and the mixture was stirred at ambient temperature for 4.5 hours. N,O-Dimethylhydroxylamine hydrochloride (1 g), triethylamine (3.2 ml) and dichloromethane (5 ml) were added, the mixture was stirred at ambient temperature for 19 hours, then it was poured into water (60 ml). The product was extracted into dichloromethane (2×30 ml), the combined extracts were dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using dichloromethane as eluant. Appropriate fractions were combined and the solvent removed in vacuo to give N,7-dimethoxy-N-methylbenzo[b]thiophene-2-carboxamide (1.5 g) as a gum which was used without further purification.

後処理

  1. stirringthe mixture was stirred at ambient temperature for 19 hours
  2. extractionThe product was extracted into dichloromethane (2×30 ml)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by flash chromatography over silica
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-994ba68bfc764de09258bba7995f7c39
出典データセット
uspto-grants-2005_05
特許番号
US06900216B2

反応ノート

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