1,2-Dichloroethane → HCID 68914541, compound

HRID 887592Notes

Reaction equation

HRID 887592 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[C:6]([NH2:8])[CH:7]=1.[CH3:10][N:11]([CH2:13][C:14](O)=[O:15])[CH3:12].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:8][C:6]1[CH:5]=[C:4]([NH:9][C:14](=[O:15])[CH2:13][N:11]([CH3:12])[CH3:10])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 673N,N-DimethylglycineHCID 733351,3-Benzenediamine, 5-chloro-HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 68914541HCID 68914541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-benzene-1,3-diamine (3 g, 21 mmol) and dimethylamino-acetic acid (2.2 g, 21 mmol) in CH2Cl2 (300 mL) was added EDC (5 g, 25 mmol), HOBt (2.9 g, 21 mmol), and DIEA (5 mL). The reaction mixture was stirred at RT for overnight. Solvent was removed in vacuum and the residue was purified through flash chromatography on silica gel (0-8% MeOH in EtOAc) to give the desired compound.

Workup

  1. customSolvent was removed in vacuum
  2. customthe residue was purified through flash chromatography on silica gel (0-8% MeOH in EtOAc)

Sources & evidence

ORD record
ord-d41f7fc725d7412ea01e43feba65b032
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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