Triethylamine → HCID 11314561, compound

HRID 1857468Notes

Reaction equation

HRID 1857468 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.[C:27]([NH2:32])([CH2:30][CH3:31])([CH3:29])[CH3:28].C(N(CC)CC)C>C(#N)C>[C:23]([NH:22][C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=[C:3]([C:2]([F:1])([F:26])[F:25])[CH:4]=1)=[N:32][C:27]([CH3:29])([CH3:28])[CH2:30][CH3:31])#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 689862-Butanamine, 2-methyl-HCID 178512266HCID 178512266, compound

Product 1

HCID 11314561HCID 11314561, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[3,5-bis(trifluoromethyl)phenyl]-N'-cyano-O-phenylisourea (0.78 mmol, 290 mg), tert-amylamine (0.85 mmol, 0.100 ml) and triethylamine (0.85 mmol, 0.119 ml) in acetonitrile (2 ml) was stirred for 25 h at 75° C. followed by work-up as described in EXAMPLE 5, b) to give the title compound (140 mg, 46%) as white crystals. Mp 149-150° C.; EI SP/MS: 366 (M+); 1H-NMR (CDCl3): δ 0.85 (t, 3H),1.35 (s, 6H), 1.75 (q, 2H), 4.65 (br s,1H), 7.70 (br s, 3H), 8.95 ppm (br s, 1H); MA calc for C15H16F6N4. 0.15 H2O: C, 49.37%; H, 4.57%; N, 14.76%. Found: C, 49.72%; H, 4.56%; N, 14.76%.

Sources & evidence

ORD record
ord-cd602964cb844c90a9765d03636eea8a
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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