Triethylamine → 3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)

HRID 1488171Notes

Reaction equation

HRID 1488171 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:22][NH:23][O:24][CH3:25].C(N(CC)CC)C>ClCCl>[CH3:25][O:24][N:23]([CH3:22])[C:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4661317(R)-Tetrahydro-3-furoic acid

Product 1

HCID 450845223-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)Yield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 250-mL round-bottom flask, was placed a solution of tetrahydrofuran-3-carboxylic acid (10 g, 86.1 mmol) in dichloromethane (200 mL). EDC.HCl (18.2 g, 94.9 mmol), N,O-dimethylhydroxylamine hydrochloride (10 g, 103 mmol) and triethylamine (24.0 mL, 172 mmol) were added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with DCM (50 mL) and washed with aqueous HCl (1 M, 3×10 mL), sodium bicarbonate (sat., 2×30 mL) and brine (3×20 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the title compound as light yellow oil (6.71 g, 49%).

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. washwashed with aqueous HCl (1 M, 3×10 mL), sodium bicarbonate (sat., 2×30 mL) and brine (3×20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43b450cd30b749d4bdf4cf800a28c1fa
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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