2,4-Difluorophenyl isocyanate → Ethyl 3-(4-(3-(2,4-difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylate

HRID 75808Notes

Reaction equation

HRID 75808 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:18].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[N:27]=[C:28]=[O:29]>O1CCCC1>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[NH:27][C:28](=[O:29])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:18]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 67353967Ethyl 3-(4-amino-3-methylphenyl)isoxazole-5-carboxylate

Product 1

HCID 67353297Ethyl 3-(4-(3-(2,4-difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(4-amino-3-methylphenyl)isoxazole-5-carboxylate (1.0 equiv.), 2,4-difluoro phenyl isocyanate (1.2 equiv.) and tetrahydrofuran in a round-bottom flask was stirred at room temperature for 48 hours. The solid precipitate was filtered and washed with a minimum quantity of THF and dried in vacuo to afford the title compound as a white solid (75%); 1H NMR (300 MHz, DMSO-d6) δ: 1.29-1.34 (t, J=7.0 Hz, 3H), 2.29 (s, 3H), 4.32-4.39 (q, 2H), 7.00-7.05 (m, 1H), 7.26-7.33 (m, 1H), 7.72-7.75 (d, J=8.4 Hz, 1H), 7.80 (s, 2H), 8.09-8.16 (m, 2H), 8.45 (s, 1H), 9.09 (s, 1H); IR (KBr) 3297, 3134, 2991, 1727, 1654, 1590, 1558, 1500, 1460, 1424, 1287, 1250, 1139, 1029, 841 cm1.

Workup

  1. filtrationThe solid precipitate was filtered
  2. washwashed with a minimum quantity of THF
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0021171d4f014ee59d09b27addfbe7da
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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