Triethylamine → 1-(o-tolyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)urea

HRID 62059

Reaction equation

HRID 62059 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]=[C:35]=[O:36].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:28]1([CH3:27])[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35]([NH:24][CH2:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=3)[N:11]=2)=[CH:16][CH:17]=1)=[O:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 904042683-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

Product 1

HCID 1186750791-(o-tolyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)ureaYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a 25 mL flask, to a solution of 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine (0.160 g, 0.442 mmol) in dichloromethane (2 mL) was added 2-methyl phenylisocyanate (0.06 g, 0.497 mmol) in dichloromethane (5 mL) followed by triethylamine (0.044 g, 0.414 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and adsorbed onto Celite®. Purification by flash column chromatography (reverse phase) 5% acetonitrile/water provided the title compound as a white solid (0.11 g, 53%).

Workup

  1. customPurification by flash column chromatography (reverse phase) 5% acetonitrile/water

Sources & evidence

ORD record
ord-7fed12727651473aadfe67fb4bbfbc95
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Linked notes

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