Methylamine → HCID 12810606, compound

HRID 2228725Notes

Reaction equation

HRID 2228725 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-])=[O:6])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:20][NH2:21]>C(Cl)Cl.CN(C=O)C.C1COCC1>[CH3:20][NH:21][C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[C:1]([O:12][CH3:13])=[O:11])=[O:6]

Participants

7

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester

Product 1

HCID 12810606HCID 12810606, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of methyl isophthalate (5.10 g, 0.028 mol) in CH2Cl2 (100 ml) at room temperature was treated with oxalyl chloride (6.0 ml) followed by DMF (3 drops). The resultant mixture was stirred under reflux (90 mins). The resultant mixture was cooled to room temperature, the solvent removed by evaporation and the residue azeotroped with CH2Cl2. The resultant mixture was dissolved in THF (100 ml), cooled to 0° C. and treated with a solution of methylamine (2M, 28 ml, 56 mmol) in THF. The mixture was allowed to warm to room temperature overnight, solvent removed by evaporation and resultant mixture was partitioned between ethyl acetate (200 ml) and water (200 ml). The organic layer separated and washed with sat aq NaHCO3, sat aq brine, and dried over MgSO4. Removal of the drying agent by filtration followed by evaporation of the solvent gave the desired product (white solid, 4.60 g, 79%). 1H NMR (CDCl3) δ 3.00 (d, 3H), 4.00 (s, 3H), 6.30 (s, br, 1H), 7.50 (t, 1H), 8.00 (d, 1H), 8.20 (d, 1H), 8.40 (s, 1H). LRMS m/z=211.1 (M+18)+.

Workup

  1. temperatureunder reflux (90 mins)
  2. customthe solvent removed by evaporation
  3. customthe residue azeotroped with CH2Cl2
  4. dissolutionThe resultant mixture was dissolved in THF (100 ml)
  5. temperatureto warm to room temperature overnight
  6. customsolvent removed by evaporation and resultant mixture
  7. customwas partitioned between ethyl acetate (200 ml) and water (200 ml)
  8. customThe organic layer separated
  9. washwashed with sat aq NaHCO3
  10. dry with materialdried over MgSO4
  11. customRemoval of the drying agent
  12. filtrationby filtration
  13. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-cc2412fca58746529604fb19642a8702
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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