HCID 178512251, compound → HCID 178457525, compound

HRID 1857473Notes

Reaction equation

HRID 1857473 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[N:18][C:19]#[N:20])OC2C=CC=CC=2)[CH:6]=[CH:7][CH:8]=1>C(#N)C.C(N)(C)C.C(N(CC)CC)C>[C:19]([NH:18][C:10]([NH:9][CH:5]([CH3:6])[CH3:4])=[N:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=1)#[N:20]

Participants

5

Reactant 1

HCID 178512251HCID 178512251, compound

Product 1

HCID 178457525HCID 178457525, compoundYield 158.6%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6363IsopropylamineSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of N-(3-trifluoromethylphenyl)-N'-cyano-O-phenylisourea (0.98 mmol, 286 mg) in dry acetonitrile (2 ml), isopropylamine (0.184 ml) and triethylamine (0.150 ml) were added. The mixture was stirred for 42 h at room temperature under nitrogen. After concentration the residue was purified by flash chromatography (ethyl acetate/heptane 1:2) to give the title compound (210 mg, 79%) as a syrup. Crystallization from ethyl acetate / heptane 1:3 gave white crystals (165 mg, 62%). Mp 109-111° C.; 1H-NMR (CDCl3): δ 1.20 (d, 6H), 4.05 (m,1H), 4.67 (br d, 1H), 7.42 (m, 1H), 7.50 (s,1H), 7.55 (m, 2H), 7.68 ppm (br, 1H); MA calc for C12H13F3N4 : C, 53.33%; H, 4.85%; N, 20.73%. Found: C, 53.61%; H, 4.92%; N, 20.67%.

Workup

  1. concentrationAfter concentration the residue
  2. customwas purified by flash chromatography (ethyl acetate/heptane 1:2)

Sources & evidence

ORD record
ord-4057f022a941415cbc4e3e2a9feb6332
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

Loading…