Triethylamine → HCID 68814398, compound

HRID 1436713Notes

Reaction equation

HRID 1436713 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[I:12][C:13]1[CH:14]=[C:15]([C:22]([N:24]([CH3:28])[CH2:25][CH2:26][CH3:27])=[O:23])[CH:16]=[C:17]([CH:21]=1)C(O)=O.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:5]([O:4][C:2](=[O:3])[C:17]1[CH:21]=[C:13]([I:12])[CH:14]=[C:15]([C:22]([N:24]([CH3:28])[CH2:25][CH2:26][CH3:27])=[O:23])[CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 68817205HCID 68817205, compound

Product 1

HCID 68814398HCID 68814398, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add benzyl chloroformate (5.96 mL, 41.77 mmol) to a solution of 5-iodo-N-methyl-N-propyl-isophthalamic acid (14.5 g, 41.77 mmol), triethylamine (6.4 mL, 45.95 mmol) and 4-dimethylaminopyridine (2.55 g, 20.88 mmol) in dichloromethane (125 mL) at 0° C. and at room temperature for 40 h. Wash the solution twice with a saturated aqueous solution of NaHCO3, 5% aqueous solution of potassium hydrogen sulfate, saturated aqueous sodium chloride, dry (magnesium sulfate), and concentrate. Dissolve the crude in dichloromethane, wash with a 0.5 N NaOH solution, H2O, saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (6 g, 33%).

Workup

  1. washWash the solution twice with a saturated aqueous solution of NaHCO3, 5% aqueous solution of potassium hydrogen sulfate, saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. dissolutionDissolve the crude in dichloromethane
  5. washwash with a 0.5 N NaOH solution, H2O, saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-2ef88f70da6043d2b35096ebff86783e
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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