Triethylamine → HCID 22728930, compound

HRID 460573Notes

Reaction equation

HRID 460573 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12]([NH:14][NH:15][C:16](=[O:18])[CH3:17])=O)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCCl>[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12]3[O:18][C:16]([CH3:17])=[N:15][N:14]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22729266HCID 22729266, compound

Product 1

HCID 22728930HCID 22728930, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution (400 ml) of N′-(4-methoxybenzo(b)furan-2-ylcarbonyl)acetohydrazide (15.6 g) in 1,2-dichloroethane were added triethylamine (21 ml) and triphenylphosphine (19.8 g) and the reaction temperature was set to 5° C. To this reaction mixture was added dropwise diethyl azodicarboxylate (40% toluene solution) (33 ml) over 15 min. The reaction temperature was set to room temperature and the mixture was stirred for 1.5 hr and washed with saturated aqueous solution of ammonium chloride. After partitioning, the obtained organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was concentrated under reduced pressure and purified by silica gel column chromatography (chloroform/ethyl acetate) to give the title compound (4.6 g) as pale-yellow crystals.

Workup

  1. customwas set to 5° C
  2. customwas set to room temperature
  3. washwashed with saturated aqueous solution of ammonium chloride
  4. customAfter partitioning
  5. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. concentrationThe obtained residue was concentrated under reduced pressure
  8. custompurified by silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-2bc65275df02486aa62f8446bda49720
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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