2-Chloroethyl isocyanate → Urea, 1-(2-chloroethyl)-3-veratryl-

HRID 32801

Reaction equation

HRID 32801 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

HCID 160352-Chloroethyl isocyanateHCID 79832Veratrylamine

Product 1

HCID 294136Urea, 1-(2-chloroethyl)-3-veratryl-Yield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. additionafter the addition
  2. concentrationIt was concentrated
  3. 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

Linked notes

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