Hydrochloric Acid → [(Methylcarbamoyl)thio]phenylacetic acid

HRID 267909

Reaktionsgleichung

Reaktionsgleichung von HRID 267909
[SH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH3:19][N:20]=[C:21]=[O:22].Cl>O.O1CCCC1>[CH3:19][NH:20][C:21]([S:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:22]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 10464709Thiomandelic acid

Produkt 1

HCID 21552790[(Methylcarbamoyl)thio]phenylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

10.08 g. (60 mM) of α-mercaptophenylacetic acid and 6.6 g. (60 mM) of triethylamine are dissolved in 50 ml. of tetrahydrofuran and 3.42 g. (60 mM) of methylisocyanate dissolved in 20 ml. of tetrahydrofuran are added dropwise with stirring. After stirring for 2 hours, the solvent is drawn off in a vacuum and the oily residue is dissolved in water. The mixture is then acidified with 2N hydrochloric acid and extracted three times each with 20 ml. of ether. After drying off the ether, 10.5 g. of white crystalline DL-[(methylcarbamoyl)thio]phenylacetic acid are obtained, which is recrystallized from ether/petroleum ether, m.p. 128°-129°.

Aufarbeitung

  1. stirringAfter stirring for 2 hours
  2. extractionextracted three times each with 20 ml
  3. dry with materialAfter drying off the ether, 10.5 g

Quellen und Nachweise

ORD-Eintrag
ord-e2ba534fe7d34e20b85588887374fb00
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03946001

Verknüpfte Notizen

Wird geladen…