Methylamine → HCID 18407197, compound

HRID 1016571Notes

Reaction equation

HRID 1016571 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[O:13]([C:15]1[CH:35]=[CH:34][CH:33]=[CH:32][C:16]=1[CH2:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:14].[CH:36]([N:39](C(C)C)CC)(C)C.CN>C(Cl)Cl>[CH3:14][O:13][C:15]1[CH:35]=[CH:34][CH:33]=[CH:32][C:16]=1[CH2:17][N:18]([C:5]([NH:39][CH3:36])=[O:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 18407190HCID 18407190, compound

Product 1

HCID 18407197HCID 18407197, compoundYield 220.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 751 mg of triphosgene in 14 ml of methylene chloride was added dropwise a solution of 2.03 g of N-(2-methoxylbenzyl)-2-phenoxyaniline and 1.03 g of diisopropylethylamine in 25 ml of methylene chloride with stirring, followed by stirring at room temperature for 5 minutes. Into the solution was blown an excess amount of methylamine with stirring, followed by stirring at room temperature for 5 minutes. After concentration under reduced pressure, the reaction mixture was poured into ethyl acetate, washed with 5% hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the precipitated crystals were recrystallized from ethyl acetate to give 2.02 g of N-(2-methoxybenzyl)-N-(N-methylaminocarbonyl)-2-phenoxyaniline.

Workup

  1. stirringby stirring at room temperature for 5 minutes
  2. stirringwith stirring
  3. stirringby stirring at room temperature for 5 minutes
  4. concentrationAfter concentration under reduced pressure
  5. additionthe reaction mixture was poured into ethyl acetate
  6. washwashed with 5% hydrochloric acid
  7. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. concentrationthe solvent was concentrated under reduced pressure
  11. customthe precipitated crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d2fc9cb22e7f4dcdacd2543624ee6dc8
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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