Hydroxylamine → 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-hydroxyacetamide

HRID 1808113Notes

Reaction equation

HRID 1808113 reaction equation
[Br:1][C:2]1[N:3]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]3[CH2:24][CH2:23]3)=[CH:14][CH:13]=2)[C:4]([S:7][CH2:8][C:9]([OH:11])=O)=[N:5][N:6]=1.[OH-:25].[Na+].O[NH2:28].O>C1COCC1.CO>[Br:1][C:2]1[N:3]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]3[CH2:24][CH2:23]3)=[CH:14][CH:13]=2)[C:4]([S:7][CH2:8][C:9]([NH:28][OH:25])=[O:11])=[N:5][N:6]=1

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 14798Sodium HydroxideHCID 53465279Lesinurad

Product 1

HCID 578113102-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-hydroxyacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (1.0 mmol) in THF (2 mL) and methanol (2 mL) is added to a solution of sodium hydroxide (5 mmol) and 50% aqueous hydroxyl amine (2 mL). After stirring for 1 hr at room temperature, water (4 mL) is added and the volatile solvents removed in vacuo. The solution is then neutralized to pH 7-8 by addition of HCl (1N), and the resulting precipitate isolated by filtration to provide 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-hydroxyacetamide.

Workup

  1. customthe volatile solvents removed in vacuo
  2. additionThe solution is then neutralized to pH 7-8 by addition of HCl (1N)
  3. customthe resulting precipitate isolated by filtration

Sources & evidence

ORD record
ord-68990c8a8efe460298230977d5c1cd2e
Source dataset
uspto-grants-2013_01
Patent number
US08357713B2

Reaction notes

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