2,4-Dichlorobenzylamine → HCID 22388178, compound

HRID 1072852Notes

Reaction equation

HRID 1072852 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.CN1CC[O:20][CH2:19]C1.C(#N)C.[Cl:26][C:27]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>O1CCCC1>[Cl:26][C:27]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:28]=1[CH2:29][N:30]1[C:4](=[O:6])[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[NH:1][C:19]1=[O:20]

Participants

6

Reactant 4

HCID 14852,4-DichlorobenzylamineHCID 6342AcetonitrileHCID 79724-MethylmorpholineHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 22388178HCID 22388178, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of dimethyl 2-aminoterephthalate (4.18 g), N,N′-carbonyldiimidazole (3.89 g) and N-methylmorpholine (4.0 ml) in tetrahydrofuran (30 ml) was stirred at room temperature for 21 hr. After concentration of the reaction mixture, acetonitrile (70 ml) and 2,4-dichlorobenzylamine (5.47 g) were added and the mixture was stirred at reflux temperature for 2 hr. The precipitated solid was washed with water (50 ml) and acetonitrile (50 ml) and dried to give the objective compound (4.64 g).

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux temperature for 2 hr
  3. washThe precipitated solid was washed with water (50 ml) and acetonitrile (50 ml)
  4. customdried

Sources & evidence

ORD record
ord-41124abea66d4df096ea61d849644214
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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