Iodoethane → HCID 44295837, compound

HRID 1449605Notes

Reaction equation

[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[S:14])[NH:9][CH2:10][C:11](N)=[O:12].[CH2:16](I)[CH3:17]>>[CH2:16]([S:14][C:8]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:15])[C:11](=[O:12])[CH2:10][N:9]=1)[CH3:17]

Participants

Reactant 2

HCID 6340Iodoethane

HCID 53825687HCID 53825687, compound

Product 1

HCID 44295837HCID 44295837, compoundYield 57.9%

Procedure

The title compound was prepared by the procedure described in Example 6 using 11.2 g of 2-[3-(2-tolyl)-thioureido]-acetamide and 15.6 g of ethyl iodide. Crystallization from ethyl acetate afforded the hydrochloride salt of the title compound as a white solid (6.8 g), m.p. 156°-158° C. (dec.). Anal. Calcd. for. C12H14N2O S. HCl: C, 53.23; H, 5.58; N, 10.34. Found: C, 52.96; H, 5.49; N, 10.25. Mass spectrum (EI, M.+) m/z 234. 1H-NMR (DMSO-d6 ; 400 MHz) 88.75 (broad s, 2H), 7.43 (m, 2H), 7.35 (m, 1H), 7.30 (m, 1H), 4.53 (q, 2H), 3.18-3.20 (m, 2H), and 1.29 ppm (t, 3H).

Workup

customThe title compound was prepared by the procedure
customCrystallization from ethyl acetate

Sources & evidence

ORD record: ord-ffb933669a754606920adaf6bfa199df
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599829

Reaction notes

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