3-Chloro-5-methoxybenzo[b]thiophene-2-carboxamide → 5-Methoxy-3-[[2-(4-morpholinyl)ethyl]thio]benzo[b]thiophene-2-carboxamide

HRID 2226861노트

반응식

HRID 2226861 반응식
C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.Cl[C:24]1[C:25]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:26]=2[S:27][C:28]=1[C:29]([NH2:31])=[O:30].Cl.[N:39]1([CH2:45][CH2:46][SH:47])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CN(C=O)C.C(OCC)(=O)C>[CH3:37][O:36][C:34]1[CH:33]=[CH:32][C:26]2[S:27][C:28]([C:29]([NH2:31])=[O:30])=[C:24]([S:47][CH2:46][CH2:45][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[C:25]=2[CH:35]=1

참가 물질

6

반응물 3

HCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamideHCID 123366224-Morpholineethanethiol hydrochlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

생성물 1

HCID 97986095-Methoxy-3-[[2-(4-morpholinyl)ethyl]thio]benzo[b]thiophene-2-carboxamide수율 83%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Diazabicycloundecene (DBU) (990 μL, 6.62 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (200 mg, 0.83 mmol) and 4-morpholineethanethiol hydrochloride (608 mg, 3.31 mmol) in 4 mL of DMF. The mixture is stirred at room temperature for 3 hours then diluted with ethyl acetate and washed with water followed by aqueous citric acid. NaHCO3 is added to the acidic extracts and the precipitated solids are collected and washed with water. Recrystallization from methanol:water provides 5-methoxy-3-[[2-(4-morpholinyl)ethyl]thio]benzo[b]thiophene-2-carboxamide in 83% yield; mp=158.5°-159.5° C.

후처리

  1. washwashed with water
  2. additionNaHCO3 is added to the acidic extracts
  3. customthe precipitated solids are collected
  4. washwashed with water
  5. customRecrystallization from methanol

출처 및 근거

ORD 기록
ord-0b53ad9354fd439c83954c267e1e6b75
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05350748

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