2-Bromo-2'-chloroacetophenone → HCID 23371583, compound

HRID 1899807Notes

Reaction equation

HRID 1899807 reaction equation
[CH3:1][CH:2]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:5][NH:4][C:3]1=[O:14].[CH:15]1[CH:20]=[C:19]([C:21]([CH2:23][Br:24])=[O:22])[C:18]([Cl:25])=[CH:17][CH:16]=1>C(O)C>[Br-:24].[Cl:25][C:18]1[CH:17]=[CH:16][CH:15]=[CH:20][C:19]=1[C:21]([CH2:23][N+:11]1[CH:12]=[CH:13][C:8]([C:6]2[S:7][CH:2]([CH3:1])[C:3](=[O:14])[NH:4][N:5]=2)=[CH:9][CH:10]=1)=[O:22]

Participants

4

Reactant 2

HCID 27357852-Bromo-2'-chloroacetophenoneHCID 233716186-Methyl-2-(pyridin-4-yl)-4H-1,3,4-thiadiazin-5(6H)-one

Product 1

HCID 23371583HCID 23371583, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Methyl-2-(4-pyridyl)-4H,6H-1,3,4-thiadiazin-5-one (415 mg, 2 mmol) and 2'-chlorophenacyl bromide (654 mg, 2.8 mmol) were dissolved in absolute ethanol (6 ml) and stirred at room temperature for one day. The solvent was removed under reduced pressure to obtain 1-[(2-chlorophenyl)carbonylmethyl]-4-(6-methyl-4H,6H-1,3,4-thiadiazin-5-one-2-yl)pyridinium bromide as yellow brown gum. The salt was dissolved in methanol (7 ml), gradually added with sodium borohydride (756 mg, 20 mmol) under ice cooling and stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue obtained was separated by column chromatography (dichloromethane-methanol=40:1) and purified to obtain the titled compound (621 mg) as opaline plates.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c934919e8a049f7937d9b3da4fa11e3
Source dataset
uspto-grants-1996_11
Patent number
US05574033

Reaction notes

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