1-Bromo-3-chloropropane → HCID 19418927, compound

HRID 864361Notes

Reaction equation

HRID 864361 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1C(=O)[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[Si:7]([CH3:17])([CH3:16])[CH2:6]1.C[Si]1(C)C2C=CC=CC=2[S:22](=[O:30])(=[O:29])NC1.C([Li])CCC.ClCCCBr>O1CCCC1>[CH3:16][Si:7]1([CH3:17])[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:22](=[O:30])(=[O:29])[N:5]([CH2:4][CH2:3][CH2:2][Cl:1])[CH2:6]1

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 19418915HCID 19418915, compoundHCID 194189184,4-dimethyl-3H-1,2,4-benzothiazasiline 1,1-dioxideHCID 178418339Butyllithium

Product 1

HCID 19418927HCID 19418927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,4-Dimethyl-2-(3-chloropropyl)-3H-1,2,4-benzothiazasiline 1,1-dioxide may be obtained in a manner similar to that described in Example 4 for the preparation of 3-(3-chloropropyl)-1,1-dimethyl-4-oxo-1,2,3,4-tetrahydro-3,1-benzazasiline, but using 3.2 g of 4,4-dimethyl-3H-1,2,4-benzothiazasiline 1,1-dioxide, 10.5 cm3 of n-butyllithium, 5.3 g of 1-chloro-3-bromopropane and 50 cm3 of tetrahydrofuran. After purification by flash chromatography on a silica column under a nitrogen stream at moderate pressure (0.5-1.5 bar) with a dichloromethane-cyclohexane mixture (50--50 by volume) as eluent, 1.95 g of 4,4-dimethyl-2-(3-chloropropyl) 3H-1,2,4-benzothiazasiline 1,1-dioxide are obtained.

Workup

  1. customAfter purification by flash chromatography on a silica column under a nitrogen stream at moderate pressure (0.5-1.5 bar) with a dichloromethane-cyclohexane mixture (50--50 by volume) as eluent

Sources & evidence

ORD record
ord-e11ae039387640f9b3917163ff3e1040
Source dataset
uspto-grants-1996_10
Patent number
US05563144

Reaction notes

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