Sodium Hydroxide → 2-Chloro-6-methanesulfonylmethyl-phenylamine

HRID 23389Notes

Reaction equation

HRID 23389 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:3]=1[NH:13]C(=O)C(F)(F)F.[OH-].[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:3]=1[NH2:13]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22574080N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 225740912-Chloro-6-methanesulfonylmethyl-phenylamineYield 90%

Conditions

Temperature
120 °C

Procedure

The crystalline N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-2,2,2-trifluoro-acetamide of Step 3 was taken up into 200 ml of 2N solution of sodium hydroxide and stirred and heated in an oil bath heated to 120° C. The homogeneous solution was stirred at this temperature for 90 minutes and slowly allowed to cool to room temperature. The flask was immersed in an ice bath and the suspension of the product was stirred at this temperature until all was crystalline. Filtration, washing well with water and thorough drying afforded 13.96 g of pure crystalline 2-chloro-6-methanesulfonylmethyl-phenylamine (90%).

Workup

  1. temperatureheated in an oil bath
  2. stirringThe homogeneous solution was stirred at this temperature for 90 minutes
  3. temperatureto cool to room temperature
  4. customThe flask was immersed in an ice bath
  5. additionthe suspension of the product
  6. stirringwas stirred at this temperature until all was crystalline
  7. filtrationFiltration
  8. washwashing well with water
  9. customthorough drying

Sources & evidence

ORD record
ord-ffe6f370f9a649a1b163cc5fc18bcff1
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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