Acetyl chloride → 5-Acetylamino-N-methyl-N-propyl-isophthalamic acid methyl ester

HRID 732516Notes

Reaction equation

HRID 732516 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([NH2:17])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27].CNN(CCC)NC>ClCCl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([NH:17][C:26](=[O:28])[CH3:27])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 56982963N,N-dimethylaminopropylamineHCID 688147595-Amino-N-methyl-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 688149295-Acetylamino-N-methyl-N-propyl-isophthalamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 5-amino-N-methyl-N-propyl-isophthalamic acid methyl ester (1.64 g, 6.55 mmol) in dichloromethane (20 mL) and add triethylamine (0.993 g, 9.83 mmol), then acetyl chloride (772 mg, 9.83 mmol). Stir at room temperature for 1 h, add N,N-dimethylamino propylamine (0.5 mL), stir 10 min, dilute with dichloromethane, wash with 1 N HCl and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate to give the title compound as a solid.

Workup

  1. stirringstir 10 min
  2. washwash with 1 N HCl and saturated aqueous sodium chloride
  3. dry with materialDry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-45caf774e5c34ab7b5630e6d19e586a5
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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