Trifluoroacetic acid → alpha-[(Thioxomethyl)amino]benzeneacetic acid
Reaction equation
[S:1]=[CH:2][NH:3][CH:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:5]([O:7]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[S:1]=[CH:2][NH:3][CH:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:5]([OH:7])=[O:6]Participants
4
Procedure
3.61 g. (0.01 mol.) of α-[(thioxomethyl)amino]benzeneacetic acid, diphenylmethyl ester, are added to a mixture of 30 ml. of trifluoroacetic acid and 5 ml. of anisole at 0°-5° and the mixture is stirred for 10 minutes. The mixture is concentrated, sodium bicarbonate solution is added to the residue and the aqueous phase is extracted with ether. This is then layered over with fresh ether, acidified and the aqueous phase is extracted twice with ether. Concentration of the ether solution yields α-[(thioxomethyl)amino]benzeneacetic acid as an oily residue.
Workup
- concentrationThe mixture is concentrated
- additionsodium bicarbonate solution is added to the residue
- extractionthe aqueous phase is extracted with ether
- extractionthe aqueous phase is extracted twice with ether
Sources & evidence
- ORD record
- ord-218d4094a40b40079a417f4366ab0156
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962229
Reaction notes
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