Triethylamine → 4-[1-(4-pentafluoroethyloxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzoyl azide

HRID 1424719Notes

Reaction equation

HRID 1424719 reaction equation
[F:1][C:2]([F:28])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].C1(P([N:43]=[N+:44]=[N-:45])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CC(O)(C)C>[F:28][C:2]([F:1])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([N:43]=[N+:44]=[N-:45])=[O:25])=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:5])([F:6])[F:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 782101774-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid

Product 1

HCID 866333834-[1-(4-pentafluoroethyloxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzoyl azide

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 4-[1-(4-pentafluoroethyloxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzoic acid (1.67 g, 4.2 mmol), diphenylphosphoryl azide (1.26 g, 4.58 mmol) and triethylamine (0.5 g, 5 mmol) in dry t-BuOH (10 mL) was heated to 75° C. for 90 min, resulting in dissolution of the starting acid and subsequent precipitation of the azide. The cooled solution was then poured onto ice (10 g), and the resulting mixture was filtered and dried to furnish the azide (0.80 g) as a white solid: mp 112-115° C. dec; 1H NMR (300 MHz, CDCl3) δ 8.62 (s, 1H), 8.33 (d, J=8.4 Hz, 2H), 8.16 (d, J=8.4 Hz, 2H), 7.85 (d, J=9 Hz, 2H), 7.42 (d, J=9 Hz, 2H); ESIMS m/z 425 (M+H).

Sources & evidence

ORD record
ord-8a0b0c0505a646ccbc536076369c48b7
Source dataset
uspto-grants-2015_01
Patent number
US08927729B2

Reaction notes

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