Ammonia → N'-[[1-(4-(aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1H-pyrazol-3-yl]methyl]-N'-hydroxyurea

HRID 1057790Notes

Reaction equation

HRID 1057790 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:23][N:24]([C:35]([O:37]C3C=CC=CC=3)=O)[O:25]C(OC3C=CC=CC=3)=O)=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH3:44]>C(O)C>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:23][N:24]([OH:25])[C:35](=[O:37])[NH2:44])=[N:12]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12052545[[1-[4-(Aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1h-pyrazol-3-yl]methyl]-n,o-bis(phenoxycarbonyl)hydroxylamine

Product 1

HCID 10137015N'-[[1-(4-(aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1H-pyrazol-3-yl]methyl]-N'-hydroxyurea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound from Step 5 (6.0 g, 9.7 mmol) was dissolved in 150 mL of ethanol and the solution was saturated with ammonia. The solution was let stand undisturbed overnight and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1 N HCl and brine, dried over anhyd. MgSO4, filtered and concentrated in vacuo to afford N′-[[1-(4-(aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1H-pyrazol-3-yl]methyl]-N′-hydroxyurea as a white solid that was crystallized from a mixture of ethyl acetate and hexane: mp 216-218° C.

Workup

  1. customstand undisturbed overnight
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1 N HCl and brine
  5. customdried over anhyd
  6. filtrationMgSO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42da318151f34321a7fdd2bd63278c2b
Source dataset
uspto-grants-2003_02
Patent number
US06515014B2

Reaction notes

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