Triethylamine → HCID 59760055, compound

HRID 1879120Notes

Reaction equation

HRID 1879120 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:13]([C:14]([OH:16])=O)=[C:12]([F:17])[C:11]([O:18][CH3:19])=[CH:10][CH:9]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O.O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:14]([C:13]2[C:8]([Cl:7])=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[F:17])=[O:16])=[CH:26][CH:25]=1)[CH3:32]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 38560396-Chloro-2-fluoro-3-methoxybenzoic acid

Product 1

HCID 59760055HCID 59760055, compoundYield 94.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (193 μl, 2.21 mmol) was added dropwise to a solution of 6-chloro-2-fluoro-3-(methyloxy)benzoic acid (300 mg, 1.47 mmol) in dichloromethane (5 ml). To this was added dimethylformamide (1 drop) and the reaction was stirred at room temperature for 3 hrs. The solvent was evaporated to afford a yellow semi-solid. This semi-solid was dissolved in dichloromethane (5 ml) and ethyl (4-aminophenyl)acetate (316 mg, 1.76 mmol) followed by triethylamine (287 μl, 2.06 mmol) were added. The resultant solution was stirred at room temperature overnight. The reaction was diluted with water and the phases separated. The organic layer was dried (Na2SO4), the solvent evaporated and the residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→50% ethyl acetate/petrol) to afford the title as a yellow semi-solid (506 mg, 94%). MS (ES+) m/z 366 [M+H+] (C18H1735ClFNO4).

Workup

  1. customThe solvent was evaporated
  2. customto afford a yellow semi-solid
  3. additionwere added
  4. customthe phases separated
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent evaporated
  7. customthe residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-25cb468d47474fd88cd11393199e1a9a
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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