3-Iodoaniline → HCID 90387378, compound

HRID 631769Notes

Reaction equation

HRID 631769 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N:20]=[C:21]=[O:22]>ClCCCl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[NH:20][C:21]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[CH:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 122713-IodoanilineHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanate

Product 1

HCID 90387378HCID 90387378, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-iodoaniline (438 mg, 2.0 mmol) in 15.0 mL 1,2-dichloroethane at rt was added 2-fluoro-5-(trifluoromethyl)phenyl isocyanate (0.304 mL, 2.1 mmol). After 4 hours the precipitant was filtered and rinsed with 10% EtOAc/hexane to give the title compound as a white solid (602 mg, 71%). 1H NMR (DSMO-d6) δ: 9.25 (br. s, 1H), 8.91 (br. s, 1H), 8.57 (dd, J=7.3, 2.1 Hz, 1H), 8.04 (t, J=1.9 Hz, 1H), 7.46-7.54 (m, 1H), 7.42 (dd, J=4.5, 2.2 Hz, 1H), 7.35-7.40 (m, 1H), 7.28-7.33 (m, 1H), 7.06-7.14 (m, 1H)

Workup

  1. filtrationAfter 4 hours the precipitant was filtered
  2. washrinsed with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-71fcef6e206249119a846a16b5c9ba35
Source dataset
uspto-grants-2016_04
Patent number
US09321721B2

Reaction notes

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