Sodium hydride → (trans)-N-[[2-(3-methoxyphenyl)cyclopropyl]methyl]butanamide

HRID 1419949Notes

Reaction equation

HRID 1419949 reaction equation
CO[N:3]([CH3:17])[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=O.[H-].[Na+].[I-].C[S+](C)(C)=[O:23].CON(C)[C:29](=O)/[CH:30]=[CH:31]/C1C=CC=C(OC)C=1.[NH4+].[Cl-]>CS(C)=O.C(OCC)(=O)C>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C@@H:7]2[CH2:8][C@H:6]2[CH2:4][NH:3][C:17](=[O:23])[CH2:29][CH2:30][CH3:31])[CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 22347586HCID 22347586, compoundHCID 53772372(trans)-N-Methoxy-N-methyl-2-(3-methoxyphenyl)cyclopropanecarboxamide

Product 1

HCID 15860309(trans)-N-[[2-(3-methoxyphenyl)cyclopropyl]methyl]butanamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(trans)-N-Methoxy-N-methyl-2-(3-methoxyphenyl) cyclopropanecarboxamide: To a suspension of NaH (16.27 g, 0.68 mol) in DMSO (375 mL) was added solid trimethylsulfoxonium iodide (149.16 g, 0.68 mol) in small portions. After the foaming had subsided (40 min), a solution of (trans)-N-methoxy-N-methyl-3-(3-methoxyphenyl)-2-propenamide (50 g, 0.23 mol) in DMSO (50 mL) was added dropwise, maintaining the temperature between 35°-40° C. Stirring was continued for 18 h at room temperature, followed by the dropwise addition of saturated NH4Cl (400 mL) and extraction with ethyl acetate. The organics were combined, washed with brine, dried (K2CO3), and concentrated to give a red oil which was then purified by Kugelrohr distillation (130° C., 0.5 mm Hg) to afford the title compound as a white wax (52.47 g, 100%): 1H NMR (300 MHz, CDCl3) δ 0.82-0.88 (m, 1H), 1.20-1.30 (m, 1H), 1.59-1.62 (m, 1H), 2.40-2.45 (m, 1H), 3.22 (s, 3H), 3.68 (s, 3H), 3.79 (s, 3H), 6.61-6.72 (m, 3H), 7.18 (t, J=6.0 Hz, 1H).

Workup

  1. custom(40 min)
  2. temperaturemaintaining the temperature between 35°-40° C
  3. washwashed with brine
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated
  6. customto give a red oil which
  7. distillationwas then purified by Kugelrohr distillation (130° C., 0.5 mm Hg)

Sources & evidence

ORD record
ord-d247ae2cd3b8489b917d6552422efb96
Source dataset
uspto-grants-1999_03
Patent number
US05889031

Reaction notes

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