Triethylamine → HCID 9821211, compound

HRID 1857467Notes

Reaction equation

HRID 1857467 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.[NH2:27][CH:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:29].C(N(CC)CC)C>C(#N)C>[C:23]([NH:22][C:14]([NH:13][C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:26])[F:25])[CH:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:6]=1)=[N:27][CH:28]([CH3:29])[C:30]([CH3:33])([CH3:32])[CH3:31])#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5209072-Butanamine, 3,3-dimethyl-HCID 178512266HCID 178512266, compound

Product 1

HCID 9821211HCID 9821211, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[3,5-bis(trifluoromethyl)phenyl]-N'-cyano-O-phenylisourea (0.8 mmol, 300 mg), 2-amino-3,3-dimethylbutane (0.88 mmol, 0.09 g) and triethylamine (0.88 mmol, 0.123 ml) in acetonitrile (2 ml) was stirred for 8 h at 75° C. After concentration the residue was purified by column chromatography (heptane:ethyl acetate 2:1) to give the title compound (140 mg, 46%) as white crystals. Mp 165.5-166.5° C.; EI SP/MS: 380 (M+); 1H-NMR (CDCl3): δ 0.92 (s, 9H),1.13 (d, 3H), 3.8 (m, 1H), 4.8 (br d, 1H), 7.74 (br s, 3H), 8.5 ppm (br, 1H); MA calc for C16H18F6N4 : C, 50.53%; H, 4.77%; N, 14.73%. Found: C, 50.48%; H, 4.74%; N, 14.45%.

Workup

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

Sources & evidence

ORD record
ord-d5ec66115c104966a22b4e6694e20452
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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