1,2-Dichloroethane → HCID 68914541, compound

HRID 887626Notes

Reaction equation

HRID 887626 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[C:6]([NH2:8])[CH:7]=1.C(Cl)CCl.C1C=CC2N([OH:23])N=NC=2C=1.[CH3:24][CH2:25][N:26]([CH:30](C)C)[CH:27](C)C>C(Cl)Cl>[NH2:8][C:6]1[CH:5]=[C:4]([NH:9][C:24](=[O:23])[CH2:25][N:26]([CH3:30])[CH3:27])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 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-AcOH (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 overnight. Solvent was removed in vacuo 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 vacuo
  2. customthe residue was purified through flash chromatography on silica gel (0-8% MeOH in EtOAc)

Sources & evidence

ORD record
ord-a98ce5af31424232accf4dd7553a73c5
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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