Diisopropylethylamine → 4-(4-Chlorobenzyl)oxazolidin-2-one

HRID 548633Notes

Reaction equation

HRID 548633 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH:11]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH2:12][OH:13].Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:11]2[CH2:12][O:13][C:23](=[O:25])[NH:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 548289beta-Amino-4-chlorobenzenepropanol

Product 1

HCID 140021924-(4-Chlorobenzyl)oxazolidin-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (0.78 ml, 4.5 mmol, 2.25 eq) is added to a solution of 2-amino-3-(4-chlorophenyl)propan-1-ol a93 (0.37 g, 2 mmol, 1 eq) in dichloromethane (75 ml). The mixture is cooled (ice bath) and triphosgene a89 (0.30 g, 1 mmol, 0.5 eq) is added. The mixture is stirred overnight at room temperature, washed with water, with 0.1 N aqueous hydrochloric acid, dried over magnesium sulfate and concentrated in vacuo to give 0.47 g of 4-(4-chlorobenzyl)-1,3-oxazolidin-2-one a94 as a yellow oil. This oil is used in the next step without any further purification.

Workup

  1. additionis added
  2. washwashed with water, with 0.1 N aqueous hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ae201b9ae4e4708ba665c4b8534d469
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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