Propylamine → HCID 44294410, compound

HRID 1857478Notes

Reaction equation

HRID 1857478 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[N:18][C:19]#[N:20])OC2C=CC=CC=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:21]([NH2:24])[CH2:22][CH3:23]>>[C:19]([NH:18][C:10]([NH:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)=[N:24][CH2:21][CH2:22][CH3:23])#[N:20]

Participants

3

Reactant 2

HCID 7852PropylamineHCID 178512268HCID 178512268, compound

Product 1

HCID 44294410HCID 44294410, compoundYield 23%

Procedure

N-(3,5-Dichlorophenyl)-N'-cyano-O-phenylisourea (0.98 mmol, 300 mg) and n-propylamine (1 ml) was stirred in a sealed flask for 19 h at 75° C. After concentration the residue was dissolved in dichloromethane, washed with 1 N aqueous HCl (2×), water, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (ethyl acetate/heptane 1:3) to give the title compound (60 mg, 23%) as white crystals. Mp 141-143° C.; 1H-NMR (CDCl3): δ 0.92 (d, 6H), 1.58 (sextet, 2H), 3.25 (q, 1H), 5.1 (br, 1H), 7.19 (m, 2H), 7.25 (m, 1H), 7.95 ppm (br, 1H); MA calc for C11H12Cl2N4 : C, 48.73%; H, 4.46%; N, 20.66%. Found: C, 49.02%; H, 4.55%; N 20.27%.

Workup

  1. concentrationAfter concentration the residue
  2. dissolutionwas dissolved in dichloromethane
  3. washwashed with 1 N aqueous HCl (2×), water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (ethyl acetate/heptane 1:3)

Sources & evidence

ORD record
ord-a3c2ae3a19ae4630928b5520dd690997
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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