Triethylamine → HCID 68550289, compound

HRID 2359879Notes

Reaction equation

HRID 2359879 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[C:31]=1[CH2:32][NH2:33]>ClCCl>[CH3:39][O:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:30]([O:29][CH3:28])[C:31]=1[CH2:32][NH:33][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 110872-Nitrobenzoic acidHCID 62365Isobutyl chloroformateHCID 28008722,6-Dimethoxybenzylamine

Product 1

HCID 68550289HCID 68550289, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

4 g 2-nitrobenzoic acid (23.93 mmol) and 2.42 g triethylamine were dissolved in 100 mL dichloromethane, mixed with one equivalent isobutyl chloroformate (3.27 g) at 5° C. and stirring was continued for 1 hour at room temperature. Then the mixture was cooled again to 5° C., 4.02 g 2,6-dimethoxybenzylamine was added and the mixture was stirred at room temperature until the reaction was complete. For workup, the mixture was diluted with dichloromethane, washed twice each with 10% citric acid, saturated NaHCO3 and saturated NaCl solution, dried with MgSO4, filtered and concentrated, yielding 7.5 g beige solids that were reacted further directly without any further workup.

Workup

  1. stirringthe mixture was stirred at room temperature until the reaction
  2. washwashed twice each with 10% citric acid, saturated NaHCO3 and saturated NaCl solution
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a710dd14b6d14987b7217c30af471984
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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