Allyl bromide → HCID 18984426, compound

HRID 5837Notes

Reaction equation

HRID 5837 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-0dc1f01a584844b9b9fa0afdb4cd92ab
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Reaction notes

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