Hydrochloric Acid → HCID 21948210, compound

HRID 2183773Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].[C:16]([Cl:19])([Cl:18])=[CH2:17].Cl>C(Cl)Cl>[Cl:18][C:16]([Cl:19])=[CH:17][C:4]([C:3]1[C:2]([Cl:1])=[N:10][C:9]([Cl:11])=[CH:8][CH:7]=1)=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of the 2,6-dichloro-nicotinoyl chloride (1.0 g, 4.76 mmol) from the previous reaction in CH2Cl2 (5 mL) was added slowly to a cooled (0° C.) and stirred slurry solution of AlCl3 (0.64 g, 4.76 mmol) in CH2Cl2 (20 mL). After 15 min, vinylidene chloride (0.38 mL, 0.46 g, 4.76 mmol) was added to the mixture dropwise. The reaction was allowed to warm to room temperature and was stirred overnight. The mixture was then poured over ice and was acidified using 1 N HCl (15 mL). Stirring was continued for 20 min and the product was extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give 3,3-dichloro-1-(2,6-dichloro-3-pyridinyl)-2-propen-1-one (0.88 g, 68%) as a light yellow oil: 1H-NMR (CDCl3, 300 MHz) δ 8.38, d, J=8.4, 1H). 7.40 (d, J=8.4, 1H), 7.10 (s, 1H); Rf=0.51 (4:1 Hex:EtOAc).

Workup

additionwas added slowly to
temperatureto warm to room temperature
additionThe mixture was then poured over ice
stirringStirring
waitwas continued for 20 min
extractionthe product was extracted with CH2Cl2 (3×)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0747a49f5bbb4109be0db45aa7792123
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900205B2

Reaction notes

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