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

HRID 2226861ノート

反応式

HRID 2226861 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0b53ad9354fd439c83954c267e1e6b75
出典データセット
uspto-grants-1994_09
特許番号
US05350748

反応ノート

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