2,4-Dihydroxybenzaldehyde → HCID 135925163, compound

HRID 1294727Notes

Reaction equation

HRID 1294727 reaction equation
[C:1]1([NH:11][C:12](=[S:15])[NH:13][NH2:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH:16][C:17]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:18]=1[CH:19]=O.S(NN)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[OH:16][C:17]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:18]=1[CH:19]=[N:14][NH:13][C:12]([NH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[S:15]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 15303P-ToluenesulfonylhydrazideHCID 2760175N-(Naphthalen-1-yl)hydrazinecarbothioamide

Product 1

HCID 135925163HCID 135925163, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(naphth-1-yl)-3-thiosemicarbazide (26 mg, 0.12 mmol) and 2,4-dihydroxybenzaldehyde (20 mg, 0.144 mmol) in dimethylformamide (1 mL) was shaken with 4 Å molecular sieves for 60 h. PS-TsNHNH2 resin (29 mg, 0.085 mmol) was added and shaking continued for 40 h, then the resin was filtered off. The solvent was removed under vacuum and the residue dissolved in ethanol. The solvent was again removed and the process repeated to give the title compound (7 mg, 18%) as a solid. MS (ES−) m/e 336 [M−H]−.

Workup

  1. filtrationthe resin was filtered off
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue dissolved in ethanol
  4. customThe solvent was again removed

Sources & evidence

ORD record
ord-04770624d24a4cfcaa7a5d63608e18cf
Source dataset
uspto-grants-2007_07
Patent number
US07241783B2

Reaction notes

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