1,1'-Carbonyldiimidazole → N-methoxy-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide

HRID 1437580Notes

Reaction equation

HRID 1437580 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>ClCCl>[CH3:29][O:28][N:27]([CH3:26])[C:10]([CH:2]1[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1)=[O:12]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acid

Product 1

HCID 55027995N-methoxy-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamideYield 54.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydro-1-benzofuran-2-carboxylic acid (500 mg, 3.1 mmol) in anhydrous dichloromethane (20 ml), under nitrogen, was added 1,1′-carbonyldiimidazole (543 mg, 3.4 mmol). After stirring for 1 h, N,O-dimethylhydroxylamine hydrochloride (327 mg, 3.4 mmol) was added and the reaction mixture was stirred at room temperature for 18 h. The mixture was washed with hydrochloric acid (1N), followed by 10% aqueous potassium carbonate solution, and the organic phase was separated, dried (MgSO4) and concentrated in vacuo to give the title compound (352 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 h
  2. washThe mixture was washed with hydrochloric acid (1N)
  3. customthe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96c0e169bc90490ca2d4c73ad494e39f
Source dataset
uspto-grants-2009_11
Patent number
US07622500B2

Reaction notes

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