2-Chloroveratraldehyde → N-(2-chloro-3,4-dimethoxybenzylideneamino)-N'-hydroxy-N''-phenylguanidine

HRID 860181Notes

Reaction equation

HRID 860181 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O.S([C:18]1[CH:24]=[CH:23][C:21](C)=[CH:20][CH:19]=1)(O)(=O)=O.[OH:25][NH:26][C:27]([NH:29][NH:30]C1C=CC=CC=1)=[NH:28]>CO>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[N:30][NH:29][C:27]([NH:26][OH:25])=[N:28][C:18]1[CH:24]=[CH:23][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 794452-ChloroveratraldehydeHCID 178427661HCID 178427661, compound

Product 1

HCID 86590910N-(2-chloro-3,4-dimethoxybenzylideneamino)-N'-hydroxy-N''-phenylguanidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.22 g (1.1 mmol) 2-chloro-3,4 dimethoxybenzaldehyde and 0.34 g (1 mmol) N-hydroxy-N′-phenylaminoguanidine tosylate was mixed in 7 ml methanol. The reaction mixture was refluxed for 80 min after which it was cooled down, to room temperature. The solvent was evaporated and 10 ml acetonitile was added and the solution was stirred for 1 h. The precipitate formed was filtered, washed with ether and subseqently dried. The yield of title compound 2 was 0.40 g (77%) as a crystalline solid M.p. 167–169° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 80 min after which it
  2. customThe solvent was evaporated
  3. addition10 ml acetonitile was added
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwashed with ether
  7. customsubseqently dried

Sources & evidence

ORD record
ord-bf477626a78644a384a8cc8ca00661d9
Source dataset
uspto-grants-2006_12
Patent number
US07153881B2

Reaction notes

Loading…