Iodoethane → HCID 22506183, compound

HRID 1814420Notes

Reaction equation

[C:1]1([NH:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:15][CH3:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([I:28])[CH3:27]>>[I-:28].[C:1]1([NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][N+:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)([CH2:26][CH3:27])[CH2:15][CH3:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 6340Iodoethane

HCID 9950747HCID 9950747, compound2×

Product 1

HCID 22506183HCID 22506183, compoundYield 78%

Procedure

A solution of N-phenylcarbamoyl-N′-[2-(4-chlorophenyl)ethyl]-N′-ethyl-1,3-diaminopropane (Compound 1, 13.7 mg, 0.0381 mmol) in ethyl iodide (2 ml) was refluxed for 3 h, and concentrated under vacuum to dryness. The residue was adsorbed on a plate of silica gel and the plate was developed with 17% methanol/chloroform to afford [3-(phenylureido)propyl][2-(4-chlorophenyl)ethyl]diethylammonium iodide (15.4 mg, 78%): MS(ES+) m/e 388 [M-I]+; 1H NMR (400 MHz, CDCl3) δ 8.15 (br, 1H), 7.35 (d, J=7.6 Hz, 2H), 7.16 (m, 6H), 6.90 (m, 1H), 6.54 (m, 1H), 3.50 (m, 2H), 3.33 (m, 6H), 3.25 (m, 2H), 2.96 (m, 2H), 1.91 (m, 2H), 1.28 (t, J=7.1 Hz, 6H).

Workup

concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record: ord-d9b1157dcaf4478fb44d5aa688cdda6d
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875884B1

Reaction notes

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