Triethylamine → HCID 66872525, compound

HRID 880698Notes

Reaction equation

HRID 880698 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5](N)=[C:4]([O:10][CH3:11])[CH:3]=1.C([N:14](CC)CC)C.[C:19]([CH2:23][C:24](Cl)=[O:25])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([CH:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:24]([NH2:14])=[O:25])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 106802184-Bromo-2-methoxy-6-methylaniline

Product 1

HCID 66872525HCID 66872525, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-2-methoxy-6-methyl-aniline (2.2 g, 10 mmol) and triethylamine (1.5 g, 15 mmol) in anhydrous dichloromethane (50 mL) was added dropwise tert-butylacetyl chloride (1.6 g, 12 mmol) with stirring at room temperature. The reaction mixture was stirred for 3 hours at room temperature, than the reaction mixture was diluted with dichloromethane and washed with water and dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by silica gel column (ISCO, hexane/EtOAc, 0-40%, 40 min) to give a white solid (2.8 g, 89%).

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at room temperature, than the reaction mixture
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by silica gel column (ISCO, hexane/EtOAc, 0-40%, 40 min)

Sources & evidence

ORD record
ord-d16c653df2804030aa40f00299ee3015
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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