Diethylamine → HCID 67246210, compound

HRID 2425723Notes

Reaction equation

HRID 2425723 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][C:3]=1[O:14][CH3:15].[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>S(Cl)(Cl)=O.C(OCC)(=O)C>[CH2:16]([N:18]([CH2:19][CH3:20])[C:9](=[O:11])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[C:3]([O:14][CH3:15])[CH:4]=1)([CH3:13])[CH3:12])[CH3:17]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 67245061HCID 67245061, compound

Product 1

HCID 67246210HCID 67246210, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-(4-iodo-3-methoxy-phenyl)-2-methyl-propionic acid (326 mg, 0.976 mmol, prepared by saponification of ethyl dimethyl-(3-ethoxy-4-iodophenyl)acetate, example 4) in thionyl chloride (5 mL) was heated at reflux for 1 h. It was concentrated to dryness then taken in 5 mL of tetrahydrofuran. Diethylamine (1 mL, 2 mmol, 2M solution in tetrahydrofuran) was added. The reaction mixture was stirred at room temperature overnight. It was diluted with ethyl acetate, washed with brine (1×), dried over anhydrous sodium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, IntelliFlash 280, eluting with a gradient of 5-95% ethyl acetate in hexanes) gave N,N-diethyl-2-(4-iodo-3-methoxy-phenyl)-isobutyramide (361.4 mg, 95%) as clear oil.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationIt was concentrated to dryness
  3. washwashed with brine (1×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the crude residue by flash column chromatography (silica gel, IntelliFlash 280
  7. washeluting with a gradient of 5-95% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5f7df2fae5404548b4a1b185db80573b
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

Loading…