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

HRID 1436660Notes

Reaction equation

HRID 1436660 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-51401928e11a4a7aa573dd83d4bbbbba
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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