Réaction #11042

Équation de réaction

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

Solvants

tetrahydrofurane toluene

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed for 2 h
2. 2
   Autreevaporated
3. 3
   workup.DISSOLUTIONthe residue dissolved in 200 ml toluene
4. 4
   Concentrationconcentrated
5. 5
   Autrepurified (flash chromatography: dichloromethane/acetic acid ethyl ester 10+1)
6. 6
   Autreto yield 43 g (100%)

Mode opératoire

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%).

Source