Methanesulfonyl chloride → Ethyl 2-((diphenylmethylene)amino)-2-(pyrazin-2-yl)acetate

HRID 2120610

Reaktionsgleichung

Reaktionsgleichung von HRID 2120610
CS(OC[C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)(=O)=O.CS(Cl)(=O)=O.O(CC1C=CC(CO)=CC=1)C1C=CC=CC=1.[Na].[C:35]1([C:41]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[N:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1.CN(C=O)C>[N:8]1[CH:9]=[CH:10][N:11]=[CH:12][C:7]=1[CH:43]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:42]=[C:41]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Komponenten

8

Edukt 5

HCID 31297Methanesulfonyl chlorideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 5360545SodiumHCID 11333367(4-(Phenoxymethyl)phenyl)methanolHCID 15096999Pyrazin-2-ylmethyl methanesulfonate

Produkt 1

HCID 10246971Ethyl 2-((diphenylmethylene)amino)-2-(pyrazin-2-yl)acetateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-(methanesulfonyloxymethyl)pyrazine (5 mmole), (prepared from 2′-(pyrazin-2-yl)styrene according to the procedure in EP 02257, followed by treatment with methanesulfonyl chloride, according to a procedure in Can. J. Chem. 1999, 77 (4) 463 in 20 ml THF was added dropwise to the sodium salt of ethyl N-(diphenylmethylene)glycinate (5 mmole) in 20 ml DMF cooled in an ice bath. The mixture was allowed to warm to room temperature during 4 hrs. The reaction mixture was partitioned between ether and water. The aqueous layer was separated and reextracted with ether (75 ml). The combined ethereal extracts were washed with brine and dried over MgSO4. Evaporation of the solvent afforded a residue which was chromatographed on silica and eluted with acetone:hexane (1:3) to afford 1.27 g (78%) of ethyl 2-(pyrazin-2-yl)-N-(diphenylmethylene)glycinate.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customThe reaction mixture was partitioned between ether and water
  3. customThe aqueous layer was separated
  4. washThe combined ethereal extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. customafforded a residue which
  8. customwas chromatographed on silica
  9. washeluted with acetone:hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-b2f5708a91564bf2a7c2e7a37740e7a2
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693098B2

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