Hydrochloric Acid → N-Methoxy-N-methylbenzofuran-5-carboxamide

HRID 1671314Notes

Reaction equation

HRID 1671314 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](Cl)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:13][NH:14][O:15][CH3:16].Cl.C(N(CC)CC)C>C(Cl)Cl>[CH3:16][O:15][N:14]([CH3:13])[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[CH:3][C:4]=2[CH:9]=1)=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 27762681-Benzofuran-5-carbonyl chloride

Product 1

HCID 59186071N-Methoxy-N-methylbenzofuran-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzofuran-5-carbonyl chloride (1 g, 5.54 mmol) in dry DCM (40 ml) is treated with N,O-dimethylhydroxylamine.HCl (0.594 g, 6.09 mmol) followed by triethylamine (1.930 ml, 13.84 mmol). After stirring at RT overnight, the mixture is diluted with DCM and washed with H2O, 1M HCl, 1M NaOH, brine, dried (MgSO4) and evaporated down to give a brown oil which is used without further purification; MS: m/z 206.1 [M+H]+

Workup

  1. washwashed with H2O, 1M HCl, 1M NaOH, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated down
  4. customto give a brown oil which
  5. customis used without further purification

Sources & evidence

ORD record
ord-23367186aafe462faa1f35bddd627338
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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