3,5-Bis(trifluoromethyl)benzaldehyde → HCID 178517826, compound

HRID 1667565Notes

Reaction equation

HRID 1667565 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH2:9])[N:5]=[C:4]([OH:10])[N:3]=1.[F:11][C:12]([F:26])([F:25])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[CH:16]=O>C(O)(=O)C.CCO>[F:11][C:12]([F:25])([F:26])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=1)[CH:16]=[N:9][NH:8][C:6]1[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([OH:10])[N:5]=1

Participants

5

Reactant 2

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 178514360HCID 178514360, compound

Product 1

HCID 178517826HCID 178517826, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-6-hydrazino-[1,3,5]triazin-2-ol (0.13 g, 0.0008 mol) and 3,5-bis(trifluoromethyl)benz aldehyde (0.39 g, 0.0016 mol) in abs. EtOH (10 mL), was added 1 drop of acetic acid. The reaction mixture was refluxed for 5 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by EtOAc to give red solid 0.21 g, in 72% yield, mp: 258.3° C. 1H NMR (DMSO-d6) δ 11.15 (s, 1H), 8.97 (s, 1H), 8.54 (s, 1H), 7.59 (s, 1H), 7.30 (s, 2H). 13C NMR (DMSO-d6) δ 179.0, 160.2, 149.8, 148.8, 128.3, 127.6, 125.4, 124.7.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. concentrationconcentrated
  3. customto remove solvent

Sources & evidence

ORD record
ord-dcaca714097c4b0f8ae1c9f6f7372da5
Source dataset
uspto-grants-2011_10
Patent number
US08044241B2

Reaction notes

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