2-(Methoxymethoxy)-1-phenylethanone → 5-(2,5-Difluorophenyl)-2-((methoxymethoxy)methyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

HRID 270519Notes

Reaction equation

HRID 270519 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O.[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:16]=1[C:17](=[S:20])[NH:18][NH2:19]>CCO.C(Cl)Cl>[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:16]=1[C:17]1[S:20][C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 105115712-(Methoxymethoxy)-1-phenylethanoneHCID 55279024Benzenecarbothioic acid, 2,5-difluoro-, hydrazide

Product 1

HCID 672148995-(2,5-Difluorophenyl)-2-((methoxymethoxy)methyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazoleYield 63%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 2-(methoxymethoxy)-1-phenylethanone (0.60 g, 3.33 mmol) in EtOH/DCM (3:1, 12 mL) was added 2,5-difluorobenzothiohydrazide (0.63 g, 3.33 mmol). After stirring at room temperature for 16 hours, the mixture was concentrated under reduced pressure. The brown residue was chromatographed (9:1 hexanes/ethyl acetate) to provide the product as a yellow oil (0.73 g, 63%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe brown residue was chromatographed (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-95bd4c0de5b4422bb6b801d66765f4b2
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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