Triethylamine → N-[1-[4-(1,1-Dimethylethyl)-2-ethoxyphenyl]-2-hydroxyethyl]-2,6-difluorobenzamide

HRID 2260705Notes

Reaction equation

HRID 2260705 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:6]=1[O:15][CH2:16][CH3:17])[CH2:3][OH:4].C(N(CC)CC)C.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28](Cl)=[O:29]>O1CCCC1>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28]([NH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:7][C:6]=1[O:15][CH2:16][CH3:17])[CH2:3][OH:4])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 153460922-Amino-2-(4-tert-butyl-2-ethoxyphenyl)ethanol

Product 1

HCID 15540384N-[1-[4-(1,1-Dimethylethyl)-2-ethoxyphenyl]-2-hydroxyethyl]-2,6-difluorobenzamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 23.6 g (0.10 mole) of 2-amino-2-(2-ethoxy-4-tert-butylphenyl)ethanol, 12.2 g (0.12 moles) of triethylamine and 200 ml of tetrahydrofuran was cooled and stirred, 17.7 g (0.10 mole) of 2,6-difluorobenzoyl chloride was added dropwise, and the mixture was stirred at room temperature for 5 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure to give 32.5 g of N-(2,6-difluorobenzoyl)-2-amino-2-(2-ethoxy-4-tert-butylphenyl)ethanol.

Workup

  1. temperaturewas cooled
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-67da13a1d7494f23a938526c6e103778
Source dataset
uspto-grants-1995_12
Patent number
US05478855

Reaction notes

Loading…