Triethylamine → HCID 22473796, compound

HRID 2183662Notes

Reaction equation

HRID 2183662 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

HCID 22473796HCID 22473796, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-994ba68bfc764de09258bba7995f7c39
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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