2-Amino-4-methylphenol → N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amine

HRID 30904

Reaktionsgleichung

Reaktionsgleichung von HRID 30904
BrC1C=CC(N=C=S)=CC=1.NC1C=C(C)C=CC=1O.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[OH:38])=S)=[CH:23][CH:22]=1.Cl.CN(C)CCCN=C=NCC>C(O)C.CCOCC>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]2[O:38][C:32]3[CH:33]=[CH:34][C:35]([CH3:37])=[CH:36][C:31]=3[N:30]=2)=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 72642-Amino-4-methylphenolHCID 161334-Bromophenyl isothiocyanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21985832N-(4-bromophenyl)-N'-(2-hydroxy-5-methylphenyl)thiourea

Produkt 1

HCID 21985825N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In a 250-mL round-bottom flask, 1-bromo-4-isothiocyanatobenzene (4.28 g, 20 mmol) and 2-amino-4-methyl-phenol (2.46 g, 20 mmol) were stirred in 120 mL ethanol at rt overnight. The formation of N-(4-bromophenyl)-N′-(2-hydroxy-5-methylphenyl)thiourea was confirmed by LC-MS. To the mixture, 1.5 eq. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) was added, and the reaction was stirred at rt for another 2 h. The reaction mixture was then heated at reflux for 6 h. The mixture was cooled to rt and the solvent was removed under reduced pressure. The solid was dissolved in EtOAc and washed with 2 N aqueous HCl and H2O. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The solid obtained was ultrasonicated in 30 mL ether and filtered to give the desired compound (3.64 g, 60%). 1H NMR (400 MHz, DMSO-d6) δ 10.70 (s, 1H), 7.70 (m, 2H), 7.55 (m, 2H), 7.35 (d, 1H), 7.25 (s, 1H), 6.95 (d, 1H), 2.40 (s, 3H). LC-MS m/z 303.3 (MH+), ret. time 3.46 min.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 6 h
  3. temperatureThe mixture was cooled to rt
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe solid was dissolved in EtOAc
  6. washwashed with 2 N aqueous HCl and H2O
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent was removed under reduced pressure
  9. customThe solid obtained
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-6ec68b7d671742119a40ab019e4facc7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423156B2

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