4-Fluoroaniline → HCID 11710337, compound

HRID 1173490Notes

Reaction equation

HRID 1173490 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH3:15])[CH2:10][C:11]([OH:13])=O)=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].N=C=N.[F:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH3:15])[CH2:10][C:11]([NH:28][C:27]2[CH:29]=[CH:30][C:24]([F:23])=[CH:25][CH:26]=2)=[O:13])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2]

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 160435CarbodiimideHCID 11380252N-[4-cyano-3-(trifluoromethyl)phenyl]-N-ethylglycine

Product 1

HCID 11710337HCID 11710337, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[4-cyano-3-(trifluoromethyl)phenyl]-N-ethyl glycine, Example 91B (0.074 g, 0.25 mmol), and resin bounded carbodiimide (0.50 g, 1.26 mmol/g) was shaken in CH2Cl2 (15 mL) for 30 min, then 4-fluoroaniline (0.044 g, 0.4 mmol) was added, and the mixture was shaken for another 12 h. The resin was filtered and washed with CH2Cl2 (2×10 mL). The resulting filtrate was concentrated under vacuum. The residue was triturated with Et2O to obtain 0.018 g (11%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.42-7.39 (m, 2H), 7.06-6.99 (m, 4H), 6.85 (dd, J=9.0, 2.7 Hz, 1H), 4.10 (s, 2H), 3.64 (q, J=7.1 Hz, 2H), 1.31 (t, J=7.1 Hz, 3H); MS (APCI) m/z 366 (M+1).

Workup

  1. filtrationThe resin was filtered
  2. washwashed with CH2Cl2 (2×10 mL)
  3. concentrationThe resulting filtrate was concentrated under vacuum
  4. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-43de33685d54453cb097555d2730e6f7
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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