Hydrochloric Acid → [(Methylcarbamoyl)thio]phenylacetic acid

HRID 1579216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579216
[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-[[(methylamino)carbonyl]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-3633b96521a24385be6642f0fe23bd8d
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931170

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