Potassium Iodide → HCID 19709987, compound

HRID 725891Notes

Reaction equation

[CH2:1]([N:3]([CH2:22][CH3:23])[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:6]=1)[CH3:2].Cl.N1C=CC(CCl)=CC=1.[C:33]([O-])([O-])=[O:34].[K+].[K+].[I-].[K+].CN(C=O)C>O>[CH2:22]([N:3]([CH2:1][CH3:2])[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:6]=1[CH:33]=[O:34])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of N,N-diethyl-4-methoxy-3-(4-pyridinylmethoxy)benzamide (19.0 g), 4-picolylchloride hydrochloride (15.0 g), K2CO3 (60.0 g) and potassium iodide (5.0 g) in DMF (500 mol) was stirred at 80° C. for 2 hours and then heated to 150° C. for 15 minutes. After cooling to room temperature, the mixture was poured into 3 l of water, and extracted twice with ethyl acetate. The combined organic phases were washed with 5% Na2CO3, dried (Na2SO4) and concentrated in vacuo. High performance liquid chromatography (silica gel, eluting with 1:1 heptane:ethyl acetate) afforded 6.5 g of the product which was crystallized from heptane/acetone, m.p. 117°-118° C.

Workup

temperatureheated to 150° C. for 15 minutes
temperatureAfter cooling to room temperature
extractionextracted twice with ethyl acetate
washThe combined organic phases were washed with 5% Na2CO3
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
washHigh performance liquid chromatography (silica gel, eluting with 1:1 heptane:ethyl acetate)

Sources & evidence

ORD record: ord-c94780fb21de4c8e958db7e5998fcb4b
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05708007

Reaction notes

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