4-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile monohydrochloride monohydrate → 4-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 270631Notes

Reaction equation

HRID 270631 reaction equation
O.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH2:11][C:12]1[N:17]=[C:16]([NH:18][OH:19])[N:15]=[C:14]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[N:13]=1>C(OC(=O)C)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH2:11][C:12]1[N:17]=[C:16]([NH:18][OH:19])[N:15]=[C:14]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=2)[N:13]=1

Participants

3

Reactant 1

HCID 222816854-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile monohydrochloride monohydrate

Product 1

HCID 4864294-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrileYield 70.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound (21) (0.00227 mol) was stirred in ethylacetate (50 ml). The mixture was washed with NaHCO3 (50 ml saturated solution), then washed with brine, dried, filtered and the solvent was evaporated. The residue was crystallized from methanol, filtered off and dried, yielding 0.60 g (70.6%) of 4-[[4-[(2,6-dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile (compound 33).

Workup

  1. washThe mixture was washed with NaHCO3 (50 ml saturated solution)
  2. washwashed with brine
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from methanol
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-f688cf125a5448d287e4e8b0016167c6
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Reaction notes

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