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

HRID 2226861Notes

Reaction equation

HRID 2226861 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0b53ad9354fd439c83954c267e1e6b75
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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