Water → 2-Chloro-N-(4-tert-butylphenylmethyl)-acetamide

HRID 2390751Notes

Reaction equation

HRID 2390751 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=[O:22].O>ClCCl>[Cl:19][CH2:20][C:21]([NH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][CH:11]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 27356554-tert-Butylbenzylamine

Product 1

HCID 468371942-Chloro-N-(4-tert-butylphenylmethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of commercially available 4-tert-butylbenzylamine (8.16 g, 50 mmol) and potassium carbonate (7.95 g, 57.5 mmol) in dichloromethane (100 ml) was added drop wise a solution of 2-chloroacetyl chloride (6.21 g, 55 mmol) in dichloromethane (25 ml) at room temperature. After stirring the reaction mixture at room temperature for 30 min, the reaction mixture was refluxed for 4 h. The reaction mixture was cooled and water (100 ml) was added. The phases were separated and the organic phase was dried over MgSO4 and evaporated in vacuo. The title compound was obtained as a white crystalline material which was used in the next step without any further purification.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. temperatureThe reaction mixture was cooled
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c81367c8c694293baceac7f7ef0f5aa
Source dataset
uspto-grants-2012_09
Patent number
US08273874B2

Reaction notes

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