Carbon Disulfide → 5-Phenyl-2(3H)-benzoxazolethione

HRID 393525

Reaktionsgleichung

Reaktionsgleichung von HRID 393525
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:6]=1[OH:17].[OH-].[K+]>C(O)C>[C:11]1([C:9]2[CH:8]=[CH:7][C:6]3[O:17][C:1](=[S:3])[NH:4][C:5]=3[CH:10]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 6348Carbon DisulfideHCID 145622-Amino-4-phenylphenolHCID 14797Potassium Hydroxide

Produkt 1

HCID 30326635-Phenyl-2(3H)-benzoxazolethione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Carbon disulfide (7.7 mL) was added to a mixture of 2-amino-4-phenylphenol (1.0 g, 5.4 mmol), potassium hydroxide (0.36 g, 6.5 mmol) and ethanol (11.7 mL). The flask was fitted with a reflux condenser and the resulting mixture was placed in an oil bath at 60° C. for 16 h. After cooling to RT, the mixture was concentrated and ethyl acetate (20 mL) and 1 M hydrochloric acid (10 mL) were added to the residue. The layers were partitioned and the organic layer was washed successively with 1 M HCl, water and brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford 1.20 g (98%) which was used without further purification: 1H NMR (d6-DMSO, 400 MHz) δ 13.98 (s, 1H), 7.64-7.62 (m, 2H), 7.58-7.49 (m, 2H), 7.46-7.42 (m, 2H), 7.39-7.33 (m, 2H); 13C (d6-DMSO, 400 MHz) δ 181.2, 148.4, 140.1, 138.5, 132.7, 129.7, 128.3, 127.7, 123.4, 111.0, 109.1; MS (Cl) m/z 228.1 (M+1); HPLC retention time=3.09 min.

Aufarbeitung

  1. customThe flask was fitted with a reflux condenser
  2. concentrationthe mixture was concentrated
  3. additionethyl acetate (20 mL) and 1 M hydrochloric acid (10 mL) were added to the residue
  4. customThe layers were partitioned
  5. washthe organic layer was washed successively with 1 M HCl, water and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford 1.20 g (98%) which
  10. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-4793c1d6b3df40d483e0b6dc535151ae
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809094B2

Verknüpfte Notizen

Wird geladen…