Chloroacetyl chloride → 2-chloro-N-(2,6-dihydroxyphenyl)acetamide

HRID 2112743Notes

Reaction equation

HRID 2112743 reaction equation
OP([O-])(O)=O.[K+].OP([O-])([O-])=O.[K+].[K+].[NH2:14][C:15]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][C:16]=1[OH:22].[Cl:23][CH2:24][C:25](Cl)=[O:26]>O>[Cl:23][CH2:24][C:25]([NH:14][C:15]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][C:16]=1[OH:22])=[O:26]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 24450Potassium Phosphate, DibasicHCID 694512-AminoresorcinolHCID 516951Monobasic potassium phosphate

Product 1

HCID 100815492-chloro-N-(2,6-dihydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

KH2PO4 (17.2 g, 126.3 mmol) and K2HPO4 (8.2 g, 35.7 mmol) in 188 ml of distilled water were deoxygenated by passing argon through the mixture for 0.5 hour. 2-Aminobenzene-1,3-diol (1 g, 8.0 mmol) was added to the buffer solution and chloroacetyl chloride (0.64 ml, 8.0 mmol) was added slowly to the reaction mixture. After addition was completed, the reaction mixture was stirred at room temperature for 1.5 hours. Water was removed by freeze-drying and the residue was dissolved in 20% MeOH in DCM. The insoluble salt was removed by filtration, the solvent was evaporated to give the subtitled compound which was used without purification in the next step.

Workup

  1. customfor 0.5 hour
  2. additionwas added slowly to the reaction mixture
  3. additionAfter addition
  4. customWater was removed
  5. customby freeze-drying
  6. dissolutionthe residue was dissolved in 20% MeOH in DCM
  7. customThe insoluble salt was removed by filtration
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c4cd83cdff0343a0aeafbea1c738f57c
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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