Phenyl Isothiocyanate → 1-Phenyl-3-[4-(phenylsulfamoyl)phenyl]thiourea

HRID 889512

Reaktionsgleichung

Reaktionsgleichung von HRID 889512
C(N(CC)CC)C.[C:8]1([N:14]=[C:15]=[S:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C1COCC1>[CH:11]1[CH:12]=[CH:13][C:8]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[S:16])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 31390Sulfabenz

Produkt 1

HCID 34210331-Phenyl-3-[4-(phenylsulfamoyl)phenyl]thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (0.07 mL, 0.5 mmol) and phenyl isothiocyanate (2.1 mL, 11 mmol) were added sequentially to a solution of 4 (2.48 g, 10 mmol) in dry THF (10 mL). After heating under reflux for 48 h, all volatiles were removed under vacuum, and the resulting crude material was purified by flash chromatography on silica gel (hexanes/acetone, 3:1) to afford N-phenyl-4-[[(phenylamino)thioxomethyl]amino]benzenesulfonamide (5, also called LED209) (1.34 g, 35%) as a white solid, mp 160-162° C. 1H NMR (CD3COCD3, 300 MHz) δ 9.35 (br s, 1H), 9.30 (br s, 1H), 8.98 (br s, 1H), 7.80-7.72 (m, 4H), 7.51-7.47 (m, 2H), 7.38-7.33 (m, 2H), 7.28-7.16 (m, 5H), 7.08-7.04 (m, 1H); 13C NMR (CD3COCD3, 75 MHz) δ 180.2, 143.9, 138.9, 138.2, 135.2, 129.3 (2C), 129.1 (2C), 127.9 (2C), 125.8, 124.6 (3C), 122.8 (2C), 120.8 (2C).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 48 h
  3. customall volatiles were removed under vacuum
  4. customthe resulting crude material was purified by flash chromatography on silica gel (hexanes/acetone, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-38b261d94b1547c787c1712d9d88442a
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252841B2

Verknüpfte Notizen

Wird geladen…