alpha,alpha'-Dichloro-p-xylene → HCID 20405116, compound

HRID 2164654Notes

Reaction equation

HRID 2164654 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][CH:4]=1.[NH:11]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:12][C:13]([O:15][CH3:16])=[O:14]>C(#N)C>[CH3:21][O:20][C:18]([CH2:17][N:11]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:5][CH:4]=1)[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:19]

Participants

4

Reactant 2

HCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 428827Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetate

Product 1

HCID 20405116HCID 20405116, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of α,α'-dichloro-p-xylene (87.5 g, 0.5 mol) in acetonitrile (300 ml) was added dimethyl iminodiacetate (328.7 g, 2.04 mols), and stirred at 65° to 70° C. for 8 hours. 250 ml of acetonitrile was added thereto, and crystals formed were removed by filtration, followed by concentrating the solution. After dissolving the residue in 600 ml of ethyl acetate, the solution was washed with water (400 ml×3), then concentrated. Recrystallization of the residue from a hexane-ethyl acetate mixture solvent gave the end product (170.0 g, 80%).

Workup

  1. customcrystals formed
  2. customwere removed by filtration
  3. concentrationby concentrating the solution
  4. dissolutionAfter dissolving the residue in 600 ml of ethyl acetate
  5. washthe solution was washed with water (400 ml×3)
  6. concentrationconcentrated
  7. customRecrystallization of the residue from a hexane-ethyl acetate mixture solvent

Sources & evidence

ORD record
ord-6ddd74a86e3f488ca5e9e8a48d06b2d2
Source dataset
uspto-grants-1985_03
Patent number
US04506001

Reaction notes

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