Toluene → HCID 10309469, compound

HRID 2115270Notes

Reaction equation

HRID 2115270 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5]Cl.C1(C)C=CC=CC=1.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[O:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[C:25]3[C:21](=[C:22]([CH2:33][OH:34])[S:23][CH:24]=3)[C:20]=2[CH:35]=1>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[O:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[C:25]3[C:21](=[C:22]([CH2:33][O:34][CH2:5][CH2:4][N:3]([CH3:7])[CH3:2])[S:23][CH:24]=3)[C:20]=2[CH:35]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 10308546HCID 10308546, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 10309469HCID 10309469, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-dimethylaminoethylchloride-hydrochloride (1.8 mmoles) in 50% sodium hydroxide (3 ml), benzyltriethylammonium chloride (0.3 mmole) and toluene solution of the alcohol 14 (0.18 mmole) were added. The reaction mixture was heated under vigorous stirring and refluxing for 5 hours. Then it was cooled to room temperature, diluted with water and extracted by dichloromethane. After purifiaction by column chromatograpy an oily product was isolated.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxing for 5 hours
  3. extractionextracted by dichloromethane
  4. customAfter purifiaction by column chromatograpy an oily product was isolated

Sources & evidence

ORD record
ord-d2f143a1525146ec975079d8e9cc1d2a
Source dataset
uspto-grants-2008_10
Patent number
US07435834B2

Reaction notes

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