N,N-Dimethylaniline → HCID 136023068, compound

HRID 1456367Notes

Reaction equation

HRID 1456367 reaction equation
CN(C)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][O:15][CH2:16][C@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[C:27]3[CH:28]=[CH:29][C:30]([O:32]CC4C=CC=CC=4)=[CH:31][C:26]=3[S:25][N:24]=2)[CH2:18]1>ClCCl>[CH3:14][O:15][CH2:16][C@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[C:27]3[CH:28]=[CH:29][C:30]([OH:32])=[CH:31][C:26]=3[S:25][N:24]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 56990206HCID 56990206, compound

Product 1

HCID 136023068HCID 136023068, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-8 °C

Procedure

8.7 ml (68 mmol) of dimethylaniline and 6.9 g (0.051 mol) of aluminium chloride are added in three portions over 4 hours to a solution of 2.10 g (5.67 mmol) of (S)-5-methoxymethyl-3-[6-(phenylmethoxy)-1,2-benzisothiazol-3-yl]oxazolidin-2-one in 76 ml of dichloromethane, which solution is cooled at -8° C. The mixture is poured into ice-water and the product is extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. After purification by chromatography on a silica column with dichloromethane and methanol, in proportions of 99:1, and trituration in diisopropyl ether, 1.4 g of product are obtained.

Workup

  1. extractionthe product is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customAfter purification by chromatography on a silica column with dichloromethane and methanol

Sources & evidence

ORD record
ord-902a41c5bedf447bbc258d5c672a8047
Source dataset
uspto-grants-1998_12
Patent number
US05843975

Reaction notes

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