Triethylamine → HCID 9949363, compound

HRID 1179246Notes

Reaction equation

HRID 1179246 reaction equation
[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22])OC1C=CC=CC=1)#[N:2].Cl.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][NH2:32].C(N(CC)CC)C>C(O)(C)C>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[NH:12][C:4]1[N:3]=[C:1]([NH2:2])[N:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[F:24])[N:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 58976687HCID 58976687, compound

Product 1

HCID 9949363HCID 9949363, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-cyano-N′-(2,4-dimethoxyphenyl)-O-phenylisourea (0.10 g, 0.34 mmol), 2-fluoro-phenylhydrazine hydrochloride (0.08 g, 0.50 mmol) and triethylamine (0.01 mL, 0.68 mmol) in isopropanol (3 mL) was heated at 100° C. for 18 h and evaporated. Purification by flash chromatography (SiO2) eluted with 1:1 ethyl acetate:hexanes provided the title compound (0.10 g, 85% yield).

Workup

  1. customevaporated
  2. customPurification by flash chromatography (SiO2)
  3. washeluted with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-c389360ce99f4678b13e6620bf8f2121
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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