Chloroacetyl chloride → 2-chloro-N-(3-fluoro-2-methylphenyl)acetamide

HRID 2233162Notes

Reaction equation

HRID 2233162 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C:7]1[C:8]([CH3:14])=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:1][CH2:2][C:3]([NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[C:7]([F:6])[C:8]=1[CH3:14])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 2855533-Fluoro-2-methylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 9542492-chloro-N-(3-fluoro-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of chloroacetyl chloride (38.4 ml, 480 mmol) in ethyl acetate (100 ml) was slowly added to a vigorously-stirred mixture of 3-fluoro-2-methylaniline (60 g, 480 mmol), saturated aqueous sodium bicarbonate (400 ml), ice (ca 100 g) and ethyl acetate (400 ml). Some solid formed then dissolved. After 1 hour the mixture was evaporated to removing the ethyl acetate) and filtered, washing with water. The resulting product was dried in vacuo (94.4 g, 98%).

Workup

  1. customSome solid formed
  2. dissolutionthen dissolved
  3. customAfter 1 hour the mixture was evaporated
  4. customto removing the ethyl acetate) and
  5. filtrationfiltered
  6. washwashing with water
  7. customThe resulting product was dried in vacuo (94.4 g, 98%)

Sources & evidence

ORD record
ord-1c69227be5944ec8ba8212b6038e45aa
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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