Sodium Dithionite → 2-(2-amino-4-trifluoromethyl-phenyl)-5-(3-trifluoromethoxy-phenoxy)-2H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 623701Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[N:14]1[N:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:35])([F:34])[F:33])[CH:26]=2)=[N:15]1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(#N)C.O.[Cl-].[Na+]>[CH2:22]([O:21][C:19]([C:17]1[C:16]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:33])([F:34])[F:35])[CH:26]=2)=[N:15][N:14]([C:5]2[CH:6]=[CH:7][C:8]([C:10]([F:12])([F:13])[F:11])=[CH:9][C:4]=2[NH2:1])[N:18]=1)=[O:20])[CH3:23]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step F, 0.76 g, 1.5 mmol) in acetonitrile (30 mL) was added a solution of sodium hydrosulfite (1.31 g, 7.5 mmol) in water (20 mL). The mixture was stirred at 23° C. for 2.5 h. The reaction mixture was diluted with saturated aqueous sodium chloride solution (30 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the title compound (0.70 g) as a pale yellow solid. The title compound was used directly in the next step without further purification.

Workup

extractionextracted with ethyl acetate (2×50 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3199aca694244aa2ae26eb1cdd8f6b21
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302999B2

Reaction notes

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