Methyl Isocyanate → 2'-[[(Methylamino)carbonyl]amino]methyl-3-bromo-1,1'-biphenyl-4-methanol
Reaktionsgleichung
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([Br:17])[CH:10]=1.[CH3:18][N:19]=[C:20]=[O:21]>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[CH3:18][NH:19][C:20]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([Br:17])[CH:10]=1)=[O:21]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 68 mg (0.23 mmol) of 2'-aminomethyl-3-bromo-1,1'-biphenyl-4-methanol (Step H) in 3 mL of dry methylene chloride and 1 mL of dry dimethylformamide under nitrogen atmosphere at 0° C. was added 0.015 mL (0.25 mmol) of methyl isocyanate. The reaction mixture was stirred for 30 minutes at 0° C. then diluted with 100 mL of ethyl acetate, washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give 71 mg (88%) of the product as a white solid which was used in the next step without further purification. 1H NMR (200 MHz, CD3 OD): δ 2.64 (s, 3H), 4.20 (s, 2H), 4.69 (s, 2H), 7.16 (m, 1H), 7.22-7.43 (m, 4H), 7.50 (d, 2 Hz, 1H), 7.58 (d, 8 Hz, 1H). FAB-MS: calculated for C16H17BrN2O2 349; found 349, 351 (80%).
Aufarbeitung
- washwashed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customThe solvent was removed under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-823ad1a921854a2581bff7cb21a9d85c
- Quelldatensatz
- uspto-grants-1997_09
- Patentnummer
- US05672596
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