(4-Aminophenyl)arsonic acid → [4-(2-Bromoacetamido)phenyl]arsonic acid

HRID 531407Notes

Reaction equation

HRID 531407 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([As:8]([OH:11])([OH:10])=[O:9])[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:18][CH2:19][C:20](Br)=[O:21]>O.ClCCl>[Br:18][CH2:19][C:20]([NH:7][C:6]1[CH:1]=[CH:2][C:3]([As:8]([OH:10])(=[O:11])[OH:9])=[CH:4][CH:5]=1)=[O:21]

Participants

6

Reactant 3

HCID 7389(4-Aminophenyl)arsonic acidHCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromide

Product 1

HCID 193853[4-(2-Bromoacetamido)phenyl]arsonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

BRAA was prepared by a modification of the method described in Donoghue et al (2000) and WO 01/21628. p-Arsanilic acid (20.6 g, 95 mmol) was added in portions to a solution of sodium carbonate (20 g, 189 mmol) in water (200 mL). When all solids had dissolved, the solution was found to be pH 10, and was chilled at 4° C. for 2 hours. Bromoacetyl bromide (15 mL, 173 mmol) in dry dichloromethane (35 mL) was added in two portions, each addition followed by vigorous shaking for 2 to 3 min. The mixture was allowed to stand for a few minutes, and the lower organic layer was drained off. 4-(N-(Bromoacetyl)amino)benzenearsonic acid (BRAA) was precipitated by acidification of the solution to about pH 2-3 with the dropwise addition of 98% sulfuric acid, collected by vacuum filtration, and dried, giving BRAA as a white solid.

Workup

  1. customBRAA was prepared by a modification of the method
  2. dissolutionWhen all solids had dissolved
  3. additioneach addition
  4. waitto stand for a few minutes
  5. custom4-(N-(Bromoacetyl)amino)benzenearsonic acid (BRAA) was precipitated by acidification of the solution to about pH 2-3 with the dropwise addition of 98% sulfuric acid
  6. filtrationcollected by vacuum filtration
  7. customdried

Sources & evidence

ORD record
ord-3a8edfe38fa24a65b482489fe5117ed2
Source dataset
uspto-grants-2016_05
Patent number
US09353152B2

Reaction notes

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