Tert-Butylamine → N-tert-butyl-3-(chloromethyl)benzamide

HRID 1878328Notes

Reaction equation

HRID 1878328 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)C(C)C)C>ClCCl>[C:12]([NH:16][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([CH2:2][Cl:1])[CH:4]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 43156221N-tert-butyl-3-(chloromethyl)benzamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

3-(Chloromethyl)benzoyl chloride (20 g, 105.80 mmol) was added to cooled (−30° C.), stirred dichloromethane (60 mL). After 10 minutes stirring, a solution of tert-butylamine (11.1 ml, 105.80 mmol) and N-ethyl-N-Isopropylpropan-2-amine (36.9 mL, 211.60 mmol) in dichloromethane (30 mL) was added dropwise. After complete addition, the reaction was allowed to warm to −15° C. and stir for 90 minutes then was allowed to warm to room temperature. The reaction was concentrated under vacuum and the residue was dissolved in ethyl acetate and washed consecutively with 2M aqueous hydrochloric acid, water (×2) and brine. The organic phase was concentrated under vacuum to give the title compound (19.61 g) as a white solid.

Workup

  1. additionAfter complete addition
  2. temperatureto warm to −15° C.
  3. stirringstir for 90 minutes
  4. temperatureto warm to room temperature
  5. concentrationThe reaction was concentrated under vacuum
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed consecutively with 2M aqueous hydrochloric acid, water (×2) and brine
  8. concentrationThe organic phase was concentrated under vacuum

Sources & evidence

ORD record
ord-2bbc978de6ca4f6890c9e69561dbb808
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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