Reaktion #11042

Reaktionsgleichung

o-phenylendiamine

ethyl 3-{[(3′-amino[1,1′-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate

thiophosgene

→

Ethyl 3-{[(3′-{[(2-aminoanilino)carbothioyl]amino}[1,1′-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate

Lösungsmittel

tetrahydrofurane toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 2 h
2. 2
   Sonstigeevaporated
3. 3
   workup.DISSOLUTIONthe residue dissolved in 200 ml toluene
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified (flash chromatography: dichloromethane/acetic acid ethyl ester 10+1)
6. 6
   Sonstigeto yield 43 g (100%)

Vorschrift

31.84 g (75 mmol) ethyl 3-{[(3′-amino[1,1′-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate 10.1.2 were dissolved in 600 ml toluene and 8.62 g thiophosgene were added. The mixture was refluxed for 2 h, evaporated and the residue dissolved in 200 ml toluene. This solution was added dropwise to a solution of o-phenylendiamine (12.2 g 113 mmol) in 500 ml tetrahydrofurane/toluene (1/1) at 40° C. The mixture was stirred for 12 h at room temperature, concentrated and purified (flash chromatography: dichloromethane/acetic acid ethyl ester 10+1) to yield 43 g (100%).

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