2-Chloroethyl isocyanate → Urea, 1-(2-chloroethyl)-3-veratryl-
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].[Cl:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][NH:7][C:17]([NH:16][CH2:15][CH2:14][Cl:13])=[O:18])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,4-dimethoxybenzylamine (2 g, 12 mmol) in anh. THF (25 mL), at r.t., under N2, was added 2-chloroethyl isocyanate (1.02 mL, 1 eq). The reaction was complete after the addition. It was concentrated and the residue was purified by flash chromatography (silica gel, cHex/EtOAc 1:1→7:3 EtOAc/NH3 (0.5 in MeOH)) to give the title compound as a white solid (2.9 g, 89%).
Workup
- additionafter the addition
- concentrationIt was concentrated
- customthe residue was purified by flash chromatography (silica gel, cHex/EtOAc 1:1→7:3 EtOAc/NH3 (0.5 in MeOH))
Sources & evidence
- ORD record
- ord-e69fce8ef4b84bd48c72d548419d365d
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07427630B2
Reaction notes
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