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

HRID 1920995Notes

Reaction equation

HRID 1920995 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.O.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

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 10331Benzofuran-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochloride

Product 1

HCID 6603722-Benzofurancarboxamide, N-methyl-Yield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzofurancarboxylic acid (1.62 g, 10 mmole), methylamine hydrochloride (0.79 g, 10 mmole), triethylamine (3.1 mL, 22 mmole), and HOBt.H2O (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% MeOH/CH2Cl2) 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-9878650b3d8941188d9c430505be2ae1
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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