Benzoyl isocyanate → Ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate

HRID 63925Notes

Reaction equation

HRID 63925 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)=[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:27]([N:35]=[C:36]=[O:37])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.CC(=O)OCC.O>[C:27]([NH:35][C:36](=[O:37])[NH:1][C:2]1[O:3][C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)=[C:5]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 2

HCID 78210Benzoyl isocyanateHCID 118863120HCID 118863120, compound

Product 1

HCID 118863090Ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylateYield 22.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-amino-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate (38.9 mg, 0.1 mmol) in toluene (5 mL) was added benzoyl isocyanate (14.7 mg, 0.1 mmol). The reaction was stirred at RT for 2 h then diluted with EA (5 mL) and water (2 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate (12 mg, 22% yield) as a white solid. 1H NMR (DMSO-d6) δ: 12.41 (s, 1H), 11.51 (s, 1H), 8.10 (d, J=7.4 Hz, 2H), 7.75 (t, J=7.5 Hz, 1H), 7.63 (t, J=7.7 Hz, 2H), 7.60-7.51 (m, 3H), 7.48 (d, J=6.9 Hz, 1H), 7.42 (d, J=8.5 Hz, 2H), 7.27 (d, J=8.3 Hz, 2H), 4.34 (s, 2H), 4.28 (q, J=7.1 Hz, 2H), 1.23 (t, J=7.1 Hz, 3H). LCMS: MH+ 537 and TR=2.962 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated to a residue which
  3. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-ada5bc4cbea8475a8ad524229761b18c
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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