Water → 2-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene

HRID 483690Notes

Reaction equation

HRID 483690 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.[CH3:19][S:20]C.O>CCOCC>[CH3:19][S:20][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 99037352-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5,6,7 or 8-bromo-2-(di-n-propylamino)tetralin (1.4 g; 4.5 mmol) in dry ether (20 ml) was cooled to -78° C. under nitrogen atmosphere. S-BuLi (7 ml, 10 mmol) was added and the mixture was stirred for 1 hr. Methylsulphide (0.31 g; 5 mmol) was added and the mixture was stirred for 3 hr. When the temperature reached -10° C., water was added. Workup afforded the product.

Workup

  1. stirringthe mixture was stirred for 3 hr
  2. customreached -10° C.
  3. customWorkup afforded the product

Sources & evidence

ORD record
ord-7d81b2547be64979baf2d3bf315b7b39
Source dataset
uspto-grants-1993_07
Patent number
US05225596

Reaction notes

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