4-(Benzo(b)thienyl)acetic acid → HCID 3087825, compound

HRID 704770Notes

Reaction equation

HRID 704770 reaction equation
[CH:1]1[CH:9]=[C:8]2[C:4]([CH:5]=[CH:6][S:7]2)=[C:3]([CH2:10][C:11]([OH:13])=O)[CH:2]=1.[CH3:14][NH:15][C@@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][C@H:17]1[N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1>[N:25]1([C@@H:17]2[CH2:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:16]2[N:15]([CH3:14])[C:11](=[O:13])[CH2:10][C:3]2[C:4]3[CH:5]=[CH:6][S:7][C:8]=3[CH:9]=[CH:1][CH:2]=2)[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 758334-(Benzo(b)thienyl)acetic acidHCID 14126789HCID 14126789, compound

Product 1

HCID 3087825HCID 3087825, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 0.5 g of 4-thianaphthene-acetic acid, 0.422 g of carbonyldimmidazole and 20 ml of tetrahydrofuran was stirred for one hour and then a solution of 0.432 g of the product of Step B in 5 ml of tetrahydrofuran was slowly added thereto. The mixture was stirred for 31/2 hours and the tetrahydrofuran was distilled off under reduced pressure. The residue was taken up in 100 ml of ether and the solution was washed with aqueous saturated sodium bicarbonate solution, then with aqueous saturated sodium chloride solution, dried and evaporated to dryness under reduced pressure to obtain 0.61 g of trans (±)- N-[2,3-dihydro-2-(pyrrolidin-1-yl)-1H-inden-1-yl]-N-methyl-4-benzo[b]thiophene-acetamide in the form of an oil.

Workup

  1. stirringThe mixture was stirred for 31/2 hours
  2. distillationthe tetrahydrofuran was distilled off under reduced pressure
  3. washthe solution was washed with aqueous saturated sodium bicarbonate solution
  4. dry with materialwith aqueous saturated sodium chloride solution, dried
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-60bfe484078a46e8929e5b9a59f0bf88
Source dataset
uspto-grants-1991_01
Patent number
US04988727

Reaction notes

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