Isopropylamine → HCID 11267722, compound

HRID 1857469Notes

Reaction equation

HRID 1857469 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[N:22][C:23]#[N:24])OC2C=CC=CC=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:27]([NH2:30])([CH3:29])[CH3:28]>>[C:23]([NH:22][C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=[C:3]([C:2]([F:1])([F:25])[F:26])[CH:4]=1)=[N:30][CH:27]([CH3:29])[CH3:28])#[N:24]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 178512266HCID 178512266, compound

Product 1

HCID 11267722HCID 11267722, compoundYield 45%

Procedure

N-[3,5-bis(trifluoromethyl)phenyl]-N'-cyano-O-phenylisourea (0.94 mmol, 350 mg) and isopropylamine (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 crystallized from ethyl acetate and heptane to give the title compound (114 mg, 45%) as white crystals. Mp 176-182° C.; 1H-NMR (CDCl3): δ 1.25 (d, 6H), 4.07 (m, 1H), 5.5 (br d, 1H), 7.71 (br s, 1H), 7.75 (br s, 2H), 8.10 ppm (br, 1H); MA calc for C13H12F6N4 : C, 46.16%; H, 3.58%; N, 16.56%. Found: C, 46.15%; H, 3.64%; N, 16.45%.

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 crystallized from ethyl acetate and heptane

Sources & evidence

ORD record
ord-6f43cd31a33e45fb944ca247098f9f41
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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