1,2-Dichloroethane → 2-Benzofurancarboxamide, N-methyl-

HRID 1761073Notes

Reaction equation

HRID 1761073 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.Cl.CN.[CH2:16]([N:18](CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:16][NH:18][C:10]([C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)=[O:12]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 10331Benzofuran-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochloride

Product 1

HCID 6603722-Benzofurancarboxamide, N-methyl-Yield 109.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzofurancarboxylic acid (1.62 9,10 mmole), methylamine hydrochloride (0.79 g. 11 mmole), triethylamine (3.1 mL, 22 mmole), and HOBt 1H2O (1.5 g, 11 mmole) in DMF (30 mL) was added EDC (2.1 g, 11 mmole). The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel (3% MeOIVCH2Cl2) gave the title compound (1.75 g, 100%) as white solid: MS (ES) m/e 176 (M+H)+.

Workup

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with 5% NaHCO3
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b4a18a5b70849d885ecb6c586bb82d7
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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