Diisopropylethylamine → HCID 18407209, compound

HRID 2271199Notes

Reaction equation

HRID 2271199 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.[CH3:13][O:14][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.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:10][C:7]([N:18]([CH2:17][C:16]1[CH:32]=[CH:33][CH:34]=[CH:35][C:15]=1[O:14][CH3:13])[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)=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 18407190HCID 18407190, compound

Product 1

HCID 18407209HCID 18407209, compoundYield 267.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 775 mg of triphosgene in 14 ml of methylene chloride was added gradually dropwise a solution of 2.16 g of N-(2-methoxybenzyl)-2-phenoxyaniline and 1.10 g of diisopropylethylamine in 25 ml of methylene chloride with stirring, followed by stirring at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure, 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 residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:15) to give 2.57 g of N-chlorocarbonyl-N-(2-methoxybenzyl)-2-phenoxyaniline.

Workup

  1. stirringby stirring at room temperature for 15 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionpoured into ethyl acetate
  4. washwashed with 5% hydrochloric acid
  5. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe solvent was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:15)

Sources & evidence

ORD record
ord-28d655f03031446c89048a22875fcf15
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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