4-Hydroxybenzoic acid hydrazide → HCID 178515915, compound

HRID 387431Notes

Reaction equation

HRID 387431 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=O)=[CH:4][CH:3]=1.I.CS[C:15](=[NH:28])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=1>N1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:15]2[NH:28][C:6]([C:5]3[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=3)=[N:8][N:9]=2)=[CH:18][C:19]=1[C:24]([F:25])([F:26])[F:27]

Participants

4

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 1785040011-[4-chloro-3-(trifluoromethyl)phenyl]-S-methylisothiourea hydroiodide

Product 1

HCID 178515915HCID 178515915, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-hydroxybenzoic acid hydrazide (3.0 g, 19.66 mmol) and S-methyl N-[4-chloro-3-(trifluoromethyl)phenyl]isothiourea hydroiodide (7.8 g, 19.66 mmol) were suspended in 100 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours under Ar atmosphere. Then it was cooled down to ambient temperature and pyridine was removed in vacuo. The resulting yellow oil was re-dissolved in a small amount of ethyl acetate, loaded on a short pad of silica gel and eluted with 5:1 hexane/ethyl acetate, then with 100% ethyl acetate to collect the product. The product was re-purified by a second silica gel column chromatography, using ISCO system (80 g pre-packed column, 25 min run, 20% to 50% EtOAc gradient in hexane). Solvent was removed in vacuo to give the title product as a white solid (2.83 g). Yield 40.4%.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours under Ar atmosphere
  2. custompyridine was removed in vacuo
  3. dissolutionThe resulting yellow oil was re-dissolved in a small amount of ethyl acetate
  4. washeluted with 5:1 hexane/ethyl acetate
  5. customwith 100% ethyl acetate to collect the product
  6. customThe product was re-purified by a second silica gel column chromatography
  7. customISCO system (80 g pre-packed column, 25 min run, 20% to 50% EtOAc gradient in hexane)
  8. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-b2e8d5a72afe43f9be9cb1b0dd3d18fb
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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