3,5-Dichlorosalicylaldehyde → 3-Trifluoromethoxy-benzoic acid [1-(3,5-dichloro-2-hydroxy-phenyl)-methylidene]-hydrazide

HRID 1255390Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[F:12][C:13]([F:26])([F:25])[O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([NH:20][NH2:21])=[O:19]>C(O)C>[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:5]=[N:21][NH:20][C:18](=[O:19])[C:17]2[CH:22]=[CH:23][CH:24]=[C:15]([O:14][C:13]([F:12])([F:26])[F:25])[CH:16]=2)[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 3,5-dichloro-2-hydroxy-benzaldehyde (0.200, 1.05 mmol) and 3-trifluoromethoxy-benzoic acid hydrazide (0.243 g, 1.05 mmol) in ethanol (3.3 mL) was heated to 60° C. for 18 hours. The reaction mixture was cooled to room temperature to precipitate the product. The solid was collected via suction filtration and rinsed with ethanol to furnish 3-trifluoromethoxy-benzoic acid [1-(3,5-dichloro-2-hydroxy-phenyl)-methylidene]-hydrazide as an off-white solid (0.412 g, 99%): mp 180-182° C.; 1H NMR (400 MHz, DMSO) δ 12.63 (s, 1H), 12.39 (s, 1H), 8.60 (s, 1H), 8.01 (d, J=7.6 Hz, 1H), 7.91 (s, 1H), 7.76-7.63 (m, 4H); ESIMS m/z 393 ([M+H]+), 391 ([M−H]−).

Workup

temperatureThe reaction mixture was cooled to room temperature
customto precipitate the product
filtrationThe solid was collected via suction filtration
washrinsed with ethanol

Sources & evidence

ORD record: ord-f3126be4d8164dde9eb6a8eda61a8b66
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461078B2

Reaction notes

Loading…