Triethylamine → HCID 22473796, 화합물

HRID 2183662노트

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HRID 2183662 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 22473796HCID 22473796, 화합물수율 65.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-994ba68bfc764de09258bba7995f7c39
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900216B2

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