Triethylamine → HCID 58097361, compound

HRID 2067830Notes

Reaction equation

HRID 2067830 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1.C(N(CC)CC)C.[C:20]([CH2:24][C:25](Cl)=[O:26])([CH3:23])([CH3:22])[CH3:21]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([NH:10][C:25](=[O:26])[CH2:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 3294234-Bromo-2,6-dimethoxyaniline

Product 1

HCID 58097361HCID 58097361, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the crude 5-bromo-1,3-dimethoxy-2-amino-benzene from above and triethylamine (1.5 g, 15 mmol) in anhydrous dichloromethane (50 mL) was added dropwise tert-butyl acetyl chloride (1.6 g, 12 mmol) with stirring at room temperature. The reaction mixture was stirred for 3 hours at room temperature. Then the reaction mixture was diluted with dichloromethane, washed with water, 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 (3.0 g, 91%). 1H-NMR (DMSO-d6, 400 MHz): δ 8.69 (brs, 1H, exchangeable with D2O), 6.87 (s, 2H), 3.73 (s, 6H), 2.11 (s, 2H), 1.02 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at room temperature
  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-f2d8b3a07dfc439f9eeae9f0ea3b0e4d
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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