Hydrochloric Acid → N-[2-(4,5,7-trifluorobenzothiazol-2-ylthio)acetyl]-N-phenylglycine methyl ester

HRID 1940619

Reaktionsgleichung

Reaktionsgleichung von HRID 1940619
[F:1][C:2]1[C:7]2[N:8]=[C:9]([SH:11])[S:10][C:6]=2[C:5]([F:12])=[CH:4][C:3]=1[F:13].[CH3:14][O:15][C:16](=[O:29])[CH2:17][N:18]([C:25](=[O:28])[CH2:26]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Ca+2].Cl>O.[I-].[K+].CS(C)=O>[CH3:14][O:15][C:16](=[O:29])[CH2:17][N:18]([C:25](=[O:28])[CH2:26][S:11][C:9]1[S:10][C:6]2[C:5]([F:12])=[CH:4][C:3]([F:13])=[C:2]([F:1])[C:7]=2[N:8]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 21463537N-chloroacetyl-N-phenylglycine methyl esterHCID 178505914HCID 178505914, Verbindung

Produkt 1

HCID 21463552N-[2-(4,5,7-trifluorobenzothiazol-2-ylthio)acetyl]-N-phenylglycine methyl esterAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 4875Potassium IodideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To dimethylsulfoxide (DMSO; 6 ml) was added 4,5,7-trifluoro-2-mercaptobenzothiazole (442 mg, 2 mmol), N-chloroacetyl-N-phenylglycine methyl ester (479 mg, 2 mmol), calcium carbonate (276 mg, 2 mmol) and potassium iodide (20 mg) and the mixture was stirred at room temperature for 1 hour. The resultant reaction mixture was diluted with water, acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried and then evaporated to yield a residue, which was crystallized from isopropyl ether to give N-[2-(4,5,7-trifluorobenzothiazol-2-ylthio)acetyl]-N-phenylglycine methyl ester (700 mg, 82%) as a colorless powder.

Aufarbeitung

  1. customThe resultant reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customto yield a residue, which
  7. customwas crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-39e246432cb740bca20fe38fef52d529
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700819

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