HCID 178433563, compound → 4-(4-methylthiazol-5-yl) benzonitrile

HRID 2107684Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12](S)=[N:11][C:10]=2[CH3:15])=[CH:5][CH:4]=1)#[N:2]>[Ni].C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][CH:12]=[N:11][C:10]=2[CH3:15])=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Raney Nickel (1 g) was added to a solution of the product of (a) (1.2 g, 5 mmol) in absolute ethanol (120 ml) and the reactants heated at 80° C. in an autoclave for 18 hours. After cooling to ambient temperature, further Raney Nickel (1 g) was added to the reaction mixture and the reactants heated at 80° C. in an autoclave for an additional 6 hours. The reaction mixture was then filtered through Arbocel and the filtrate evaporated to dryness. The residue was flash chromatographed (Merck 60 Kieselgel-ethyl acetate:hexane:diethylamine, 25:75:2) to give the title product a gum which solidified on standing (0.36 g, 35%), and was used directly in Preparation 19.

Workup

temperatureAfter cooling to ambient temperature
temperaturethe reactants heated at 80° C. in an autoclave for an additional 6 hours
filtrationThe reaction mixture was then filtered through Arbocel
customthe filtrate evaporated to dryness
customchromatographed (Merck 60 Kieselgel-ethyl acetate:hexane:diethylamine, 25:75:2)

Sources & evidence

ORD record: ord-96a40f4ffcf1450c83568e4bd53e4c99
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935430

Reaction notes

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