Triethylamine → 4-(3-chloropropoxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide

HRID 251452Notes

Reaction equation

HRID 251452 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[Cl:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>ClCCl>[Cl:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:24])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 123892714-(3-Chloropropoxy)benzoyl chloride

Product 1

HCID 119503624-(3-chloropropoxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-2-methylpropanol (0.914 g, 10.2 mmol, 1.1 eq) and triethylamine (2.6 ml, 18.7 mmol, 2 eq) in dry dichloromethane (75 ml) is cooled (ice bath) and a solution of 4-(3-chloropropoxy)benzoyl chloride ax52 (2.95 g, 12.4 mmol, 1 eq) in dichloromethane (15 ml) is added dropwise, over 30 min. The mixture is then stirred at room temperature overnight. The suspension is washed with 1 M aqueous hydrochloric acid (2 times), an aqueous potassium carbonate solution (2 times) and brine, dried over magnesium sulfate and evaporated in vacuum to give 4-(3-chloropropoxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide ax53 (3.4 g).

Workup

  1. washThe suspension is washed with 1 M aqueous hydrochloric acid (2 times)
  2. dry with materialan aqueous potassium carbonate solution (2 times) and brine, dried over magnesium sulfate
  3. customevaporated in vacuum

Sources & evidence

ORD record
ord-e0bde742086946f7aaab396c7b178387
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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