Triethylamine → HCID 22729049, compound

HRID 460577Notes

Reaction equation

HRID 460577 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([NH:16][NH:17][C:18](=[O:20])[CH3:19])=O)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.N(C(OCC)=O)=NC(OCC)=O>ClCCCl>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]3[O:20][C:18]([CH3:19])=[N:17][N:16]=3)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22728917HCID 22728917, compound

Product 1

HCID 22729049HCID 22729049, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N′-(4-(Methoxymethyloxy)benzo(b)thiophen-2-ylcarbonyl)acetohydrazide (2.4 g) was dissolved in 1,2-dichloroethane (50 ml) and triphenylphosphine (3.2 g) and triethylamine (2 ml) were added. The mixture was stirred under ice-cooling. Diethyl azodicarboxylate (40% toluene solution) (5.2 g) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into ice water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title product (1.4 g) as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cb799a39ccba4248a094a324cb8acdc7
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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