Hydrochloric Acid → 2-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acid

HRID 992590

Reaktionsgleichung

Reaktionsgleichung von HRID 992590
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([SH:6])[CH3:5].C(N(CC)CC)C.[CH:15]1[C:25]2[C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[C:22](=[O:30])[O:21][C:20](=[O:31])[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[CH3:5][C:4]([SH:6])([CH3:7])[CH2:3][NH:2][C:22]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[C:25]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[C:20]([OH:31])=[O:21])=[O:30]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 72794Diphenic anhydrideHCID 130491041-Amino-2-methyl-2-propanethiol hydrochloride

Produkt 1

HCID 184127982-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acidAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cooled suspension of 1-amino-2-methyl-2-propanethiol hydrochloride (1.08 g, 7.62 mmol) in methylene chloride (20 mL) was added triethylamine (1.2 mL, 8.61 mmol) followed by dibenzo[c,e]oxepin-5,7-dione (1.68 g, 7.42 mmol). After stirring at room temperature for 1 h, cold 2 N HCl (50 mL) was added. After separation, the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organic layers were washed with brine and dried under sodium sulfate. The solvent was removed and the resulting residue was triturated with hexane to give the title compound as white solid (2.44 g, 98.9%). mp 150-153° C.; 1H NMR (CDCl3, 300 MHz): δ1.03 (s, 3H), 1.12 (s, 3H), 1.36 (s, 1H), 3.15 (dd, J=13.7 and 5.7 Hz, 1H), 3.38 (dd, J=13.7 and 6.9 Hz, 1H), 6.92 (t, J=6.1 Hz, 1H), 7.09-7.17 (m 2H), 7.38-7.48 (m, 4H), 7.57-7.61 (m, 1H), 7.80-7.83 (m, 1H); 13C NMR (CDCl3, 75 MHz,): δ29.36, 29.75, 44.66, 53.01, 127.28, 127.96, 128.04, 129.38, 129.93, 130.06, 130.20, 131.19, 132.02, 134.69, 138.90, 140.11, 170.99, 171.24; LCMS (m/e): 330 (M+1).

Aufarbeitung

  1. customAfter separation
  2. extractionthe aqueous layer was extracted with dichloromethane (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried under sodium sulfate
  5. customThe solvent was removed
  6. customthe resulting residue was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-31a34c28163c468a9ba5ea74de995ad3
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469065B1

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