Toluene → 5-Methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester

HRID 895335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895335
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[NH2:11].C(N(CC)CC)C.[C:20](Cl)(Cl)=[O:21].C1(C)C=CC=CC=1.[C:31]1([SH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[N-]=C=O>C1COCC1>[CH3:10][C:8]1[CH:7]=[CH:6][C:5]([NH:11][C:20]([S:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:21])=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:12]

Komponenten

8

Edukt 6

HCID 1140TolueneHCID 6371PhosgeneHCID 7969ThiophenolHCID 8471TriethylamineHCID 105034IsocyanateHCID 1201104Methyl 2-Amino-5-methylbenzoate

Produkt 1

HCID 865895625-Methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Amino-5-methylbenzoic acid methyl ester (122 mg, 0.79 mmol) and triethylamine (0.28 ml, 1.96 mmol) were dissolved in THF (10 ml). A 20% solution of phosgene in toluene (0.74 ml, 1.6 mmol) was added, causing immediate formation of a white precipitate. After 1 h, excess phosgene was purged with a stream of nitrogen, the vented gas being passed through a base scrubber. Thiophenol (81 μl, 0.79 mmol) was added to this crude isocyanate solution, which was then stirred for 1 h. The mixture was filtered to remove triethylamine hydrochloride, the solid being washed with ether. After concentration of the filtrate, the residue was purified by flash chromatography (5% to 10% EtOAc/petrol) to give 5-methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester: m/z (ES+) 300 (M−H).

Aufarbeitung

  1. customexcess phosgene was purged with a stream of nitrogen
  2. filtrationThe mixture was filtered
  3. customto remove triethylamine hydrochloride
  4. washthe solid being washed with ether
  5. customAfter concentration of the filtrate, the residue was purified by flash chromatography (5% to 10% EtOAc/petrol)

Quellen und Nachweise

ORD-Eintrag
ord-495e76e74eb444b7a49d4aad3c7e7a50
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916808B2

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