Allyl bromide → HCID 18984426, compound

HRID 1198448Notes

Reaction equation

HRID 1198448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[N:10]([CH2:22][CH2:23][CH2:24][NH:25][CH3:26])[C:9]2=[O:27])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[CH:35]=[CH2:36]>CC(C)=O>[CH2:34]([N:25]([CH2:24][CH2:23][CH2:22][N:10]1[C:9](=[O:27])[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[S:13][C:12]2[CH:14]=[CH:15][C:16]3[C:21]([C:11]1=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:26])[CH:35]=[CH2:36]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 18984401HCID 18984401, compound

Product 1

HCID 18984426HCID 18984426, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-(4-chlorophenyl)-1-[3-(methylamino)propyl]-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (1.79 g), potassium carbonate (2.18 g) and acetone (50 ml) is added allyl bromide (0.65 g) under ice cooling, and the mixture is stirred at room temperature overnight. The insoluble materials are filtered off and acetone is distilled off, and the oily residue is purified by silica gel column chromatography (eluent, chloroform: methanol=20:1) to give 1-[3-(N-allyl-N-methylamino)propyl]-3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one as oil.

Workup

  1. filtrationThe insoluble materials are filtered off
  2. distillationacetone is distilled off
  3. customthe oily residue is purified by silica gel column chromatography (eluent, chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-91643836807c45be8100323a4d453a4c
Source dataset
uspto-grants-1994_01
Patent number
US05281592

Reaction notes

Loading…