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 1062551Notes

Reaction equation

HRID 1062551 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-97a7978ffcc141c78bf0e126a2ff33c6
Source dataset
uspto-grants-2005_11
Patent number
US06962916B2

Reaction notes

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