2-Methoxyethylamine → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyethyl)urea
Reaction equation
[Si]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH2:11])(C(C)(C)C)(C)C.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH3:38][O:39][CH2:40][CH2:41][NH2:42]>C1(C)C=CC=CC=1>[OH:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH:11][C:20]([NH:42][CH2:41][CH2:40][O:39][CH3:38])=[O:22]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (200 mg, 0.75 mmol) in toluene (5 mL), triphosgene (84 mg, 0.3 mmol) and triethylamine (0.13 mL, 0.9 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-methoxyethylamine (56.3 mg, 0.75 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (95 mg, 50%). EI-MS m/z 256.2 (M+). mp: 190.0-190.7° C.
Workup
- temperatureThen it was cooled to room temperature
- customall solvent was evaporated
- dissolutionThe residue was dissolved in DMF (1 mL)
- stirringThe reaction mixture was stirred at 80° C. for 16 hours
Sources & evidence
- ORD record
- ord-e32a29067b2640b49c7c561dd85cfe3c
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06133319
Reaction notes
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