2,6-Difluorophenyl isocyanate → Ethyl 3-(4-(3-(2,6-difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylate

HRID 75802Notes

Reaction equation

HRID 75802 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]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=1[N:27]=[C:28]=[O:29]>O1CCCC1>[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[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 5221622,6-Difluorophenyl isocyanateHCID 67353967Ethyl 3-(4-amino-3-methylphenyl)isoxazole-5-carboxylate

Product 1

HCID 67352408Ethyl 3-(4-(3-(2,6-difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(4-amino-3-methylphenyl)isoxazole-5-carboxylate (1.0 equiv.), 2,6-difluoro phenyl isocyanate (1.2 equiv.) and tetrahydrofuran was taken in a round bottom flask and was stirred at room temperature for 48 hours. The solid precipitate was filtered and washed with minimum quantity of THF and dried in vacuo to afford the title compound as a white solid (91%); 1H NMR (300 MHz, DMSO-d6) δ: 1.29-1.34 (t, J=7.0 Hz, 3H), 2.31 (s, 3H), 4.33-4.40 (q, 2H), 7.11-7.17 (m, 2H), 7.24-7.31 (m, 1H), 7.71-7.74 (dd, J=8.7 Hz, 1.8 Hz, 1H), 7.81 (s, 2H), 8.04-8.07 (d, J=8.7 Hz, 1H), 8.31 (s, 1H), 8.65 (s, 1H); IR (KBr) 3292, 3132, 2984, 1723, 1644, 1621, 1588, 1560 1471, 1449, 1288, 1235, 1125, 1006, 849, 768 cm−1.

Workup

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

Sources & evidence

ORD record
ord-6f0d971996c2478d93fe5fb8f180b25c
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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