Potassium Carbonate → [5-phenoxy-(1,2,4)-thiadiazol-3-yl]-methyl (1R,3R) 2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-1-carboxylate

HRID 544440Notes

Reaction equation

HRID 544440 reaction equation
[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Br:8])[Br:7])[C@H:3]1[C:9]([OH:11])=[O:10].Cl[CH2:14][C:15]1[N:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCCOCCOCCOCCOCC1.C(C(C)=O)C>[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Br:8])[Br:7])[C@H:3]1[C:9]([O:11][CH2:14][C:15]1[N:19]=[C:18]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[S:17][N:16]=1)=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10924480Deltamethrinic acidHCID 131061443-Chloromethyl-5-phenoxy-(1,2,4)-thiadiazole

Product 1

HCID 57007880[5-phenoxy-(1,2,4)-thiadiazol-3-yl]-methyl (1R,3R) 2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-1-carboxylateYield 59.9%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3.3 g of (1R,3R) 2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-1-carboxylic acid, 2.2 g of the product of Step A, 1.5 g of potassium carbonate, 100 mg of 1,4,7,10,13,16-hexaoxacyclooctadecane and 50 ml of methyl ethyl ketone wasrefluxed for 24 hours and was evaporated to dryness under reduced pressure.The residue was added to water and the aqueous mixture was extracted with ethyl acetate. The organic phase was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution withbenzene yielded 2.84 g of [5-phenoxy-(1,2,4)-thiadiazol-3-yl]-methyl (1R,3R) 2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-1-carboxylate.

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. additionThe residue was added to water
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. customThe organic phase was evaporated to dryness under reduced pressure
  5. customthe residue was chromatographed over silica gel
  6. washElution withbenzene

Sources & evidence

ORD record
ord-041ae84039fd4bfe8db51abe152182b9
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Reaction notes

Loading…