Azide → 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazol-3-yl)phenyl)pentanoyl azide 3-(4-(1-isocyanatobutan-2-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

HRID 573847Notes

Reaction equation

HRID 573847 reaction equation
[F:1][C:2]([F:29])([F:28])[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]([CH:21]([CH2:26][CH3:27])[CH2:22][C:23]([OH:25])=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[N-:30]=[N+:31]=[N-:32].[N-:33]=[C:34]=[O:35]>>[F:28][C:2]([F:1])([F:29])[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]([CH:21]([CH2:26][CH3:27])[CH2:22][C:23]([N:30]=[N+:31]=[N-:32])=[O:25])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[N:33]([CH2:22][CH:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:29])([F:28])[F:1])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1)[CH2:26][CH3:27])=[C:34]=[O:35]

Participants

4

Reactant 3

HCID 33558AzideHCID 105034IsocyanateHCID 904041263-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)pentanoic acid

Product 1

HCID 904187603-(4-(1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazol-3-yl)phenyl)pentanoyl azide 3-(4-(1-isocyanatobutan-2-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Procedure

The title compound was prepared from 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)pentanoic acid (CA12) to furnish a mixture of azide and isocyanate, 0.723 g, 72%): 1H NMR (400 MHz, CDCl3) δ 8.56 (two s, 1H), 8.20-8.15 (m, 2H), 7.85-7.74 (m, 2H), 7.39 (dt, J=9.0, 1.0 Hz, 2H), 7.34-7.29 (m, 2H), 3.62-3.38 (m, 2H), 2.77-2.59 (m, 1H), 1.93-1.59 (m, 2H), 0.94-0.83 (m, 3H).

Workup

  1. customto furnish

Sources & evidence

ORD record
ord-6328614999de4da6a9b645720ebfc62a
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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