Triethylamine → HCID 23511749, compound

HRID 354391Notes

Reaction equation

HRID 354391 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]CC)=[O:10])=[C:4]([F:14])[C:3]=1[F:15].C(N(CC)CC)C.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]=[C:31]=[O:32]>CN(C=O)C>[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31](=[O:32])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([F:14])[C:3]=1[F:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 23511692HCID 23511692, compound

Product 1

HCID 23511749HCID 23511749, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 4-amino-2,3-difluorophenylacetate (323 mg, 1.5 mmol) in DMF (8 mL), were added triethylamine (0.209 ml, 1.5 mmol) and 2-methylphenyl isocyanate (0.372 ml, 3.0 mmol) at rt. The stirring was continued for 48 hour at 80° C. The reaction mixture was evaporated in vacuo, and the solid was suspended to n-hexane. The solid was collected through filtration. The solid was dissolved in THF—MeOH (1:1, v/v, 20 mL), and was added 4M NaOH (10 mL) at rt. The stirring was continued for 18 hours at rt. The reaction was poured into 1M HCl, and the resulting precipitate was collected through filtration. The solid was recrystallized with CHCl3-n-hexane to give 4-[(2-methylphenyl)ureido]-2,3-difluorophenylacetic acid (200 mg, 42%) as a white solid. 1H-NMR (CDCl3) δ2.30 (s, 3H), 3.35 (s, 2H), 6.98 (m, 1H), 7.04 (m, 1H), 7.18 (d, J=7.3 Hz, 2H), 7.69 (d, J=8.1 Hz, 1H), 7.90 (m, 1H); MS FAB) m/z 321 (M++1).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. filtrationThe solid was collected through filtration
  3. dissolutionThe solid was dissolved in THF—MeOH (1:1, v/v, 20 mL)
  4. additionwas added 4M NaOH (10 mL) at rt
  5. waitThe stirring was continued for 18 hours at rt
  6. additionThe reaction was poured into 1M HCl
  7. filtrationthe resulting precipitate was collected through filtration
  8. customThe solid was recrystallized with CHCl3-n-hexane

Sources & evidence

ORD record
ord-7fcf1e40d1de4c678c3274de41d277aa
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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