Acetonitrile → Benzenamine, 2-(tetradecyloxy)-

HRID 1707801Notes

Reaction equation

HRID 1707801 reaction equation
[CH2:1]([O:11][C:12]1[C:13]([C:22]([NH:24][O-:25])=[O:23])=[CH:14][C:15]2[C:20]([CH:21]=1)=CC=CC=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Na+].C[O-].[Na+].C(#[N:32])C.C(OCC)(=O)C.O1[CH2:43][CH2:42][CH2:41][CH2:40]1>>[CH2:1]([O:11][C:12]1[CH:21]=[CH:20][CH:15]=[CH:14][C:13]=1[C:22]([NH:24][OH:25])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:40][CH2:41][CH2:42][CH3:43].[CH2:1]([O:11][C:12]1[CH:21]=[CH:20][CH:15]=[CH:14][C:13]=1[NH2:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 23681993HCID 23681993, compound

Product 2

HCID 117021Benzenamine, 2-(tetradecyloxy)-HCID 18962633HCID 18962633, compound

Conditions

Temperature
60 °C

Procedure

2-Myristyloxybenzohydroxamic acid was synthesized according to the method provided in part (i) of Example 1. Thereafter, one gram of said compound was dissolved in 5 ml of tetrahydrofuran, and thereto were added 0.83 ml of sodium methylate (28 wt % methanol solution) and 20 ml of acetonitrile. The mixture was heated to 60° C. and kept there for 1.5 hours with stirring (the formation rate of the desired compound in this reaction system was found to be 100% by an analysis using high-speed liquid chromatography). The resulting solution was admixed with 50 ml of ethyl acetate, and washed once with 50 ml of saturated brine and then twice with water. The organic layer was separated from the aqueous layer, dried with Glauber's salt, and then concentrated. The residue was admixed with 5 ml of methanol, and cooled in an ice bath to precipitate white crystals. These white crystals were filtered off, washed with 0.5 ml of ice-cold methanol, and then dried. Thus, 400 mg of 2-myristyloxyaniline (Compound 3) was obtained in a 67% yield. The melting point thereof was 45.5°-46.5° C.

Workup

  1. washwashed once with 50 ml of saturated brine
  2. customThe organic layer was separated from the aqueous layer
  3. dry with materialdried with Glauber's salt
  4. concentrationconcentrated
  5. temperaturecooled in an ice bath
  6. customto precipitate white crystals
  7. filtrationThese white crystals were filtered off
  8. washwashed with 0.5 ml of ice-cold methanol
  9. customdried

Sources & evidence

ORD record
ord-b78f8d3d1c1245ccab1a7071e06480ab
Source dataset
uspto-grants-1994_10
Patent number
US05354891

Reaction notes

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