Potassium Iodide → 2-{3,5-Dichloro-4-[(5-(3-methyl-5-isothiazolyl)penyl)-oxy]phenyl}-4,5-dihydro-oxazole

HRID 359856Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[S:11][N:10]=[C:9]([CH3:12])[CH:8]=1.[I-].[K+].[Cl:15][C:16]1[CH:21]=[C:20]([C:22]2[O:23][CH2:24][CH2:25][N:26]=2)[CH:19]=[C:18]([Cl:27])[C:17]=1[OH:28].[OH-].[K+].[C:31](#N)C>>[Cl:27][C:18]1[CH:19]=[C:20]([C:22]2[O:23][CH2:24][CH2:25][N:26]=2)[CH:21]=[C:16]([Cl:15])[C:17]=1[O:28][C:2]1[CH:31]=[C:6]([C:7]2[S:11][N:10]=[C:9]([CH3:12])[CH:8]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 5

HCID 4875Potassium Iodide

HCID 6342Acetonitrile

HCID 14797Potassium Hydroxide

HCID 200639705-(5-Chloropentyl)-3-methylisothiazole

HCID 1356214662,6-Dichloro-4-(4,5-dihydro-2-oxazolyl)phenol

Product 1

HCID 1317168152-{3,5-Dichloro-4-[(5-(3-methyl-5-isothiazolyl)penyl)-oxy]phenyl}-4,5-dihydro-oxazole

Procedure

A suspension of 6.5 g 5-(5-chloropentyl)-3-methylisothiazole, 5.3 g potassium iodide, 9.1 g 2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenol and 3.9 g potassium hydroxide in 300 ml acetonitrile was heated at reflux for 40 hours. Filtration, concentration and flash filtration (silica gel; 1:1 hexane/ethyl acetate) gave 9.8 g of oily product which when crystallized from hexane at Dry Ice temperature gave 5.3 g 2-{3,5-dichloro-4-[(5-(3-methyl-5-isothiazolyl)pentyl)oxy]phenyl}-4,5-dihydro-oxazole as a colorless solid, m.p. 38°-39.5° C.

Workup

temperaturewas heated
temperatureat reflux for 40 hours
filtrationFiltration, concentration and flash filtration (silica gel; 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-78282930f2b04362ba04b7a61f5a1928
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05002960

Reaction notes

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