Triethylamine → HCID 21714406, compound
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.[Cl:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[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][C:40]1[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=1[Cl:38])=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.12 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.34 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then the reaction mixture was cooled to room temperature and all the solvent was evaporated. The residue was dissolved in DMF (1 mL). 2-chlorobenzylamine (158.6 mg, 1.12 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours Chromatography of the resulting liquid on silica gel (30% Ethyl acetate/Hexane) gave desired product (210 mg, 57%). EI-MS m/z 322.8 (M+); m.p. 199.2-199.6° C.
Workup
- temperatureThen the reaction mixture was cooled to room temperature
- customall the solvent was evaporated
- dissolutionThe residue was dissolved in DMF (1 mL)
- stirringThe reaction mixture was stirred at 80° C. for 16 hours Chromatography of the resulting liquid on silica gel (30% Ethyl acetate/Hexane)
Sources & evidence
- ORD record
- ord-1fafd678f0bb47c38d7070ef3a894f13
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271261B1
Reaction notes
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