Iodoethane → Hydrochloric Acid

HRID 1449613Notes

Reaction equation

HRID 1449613 reaction equation
[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH2:17](I)[CH3:18]>Cl>[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][N:10]=[C:9]2[S:15][CH2:17][CH3:18])[CH:5]=[CH:6][CH:7]=1.[ClH:1]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 54277983HCID 54277983, compound

Product 2

HCID 313Hydrochloric AcidYield 600.9%HCID 44295791HCID 44295791, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The title compound was prepared by the procedure described in Example 6 using 12.0 g of 2-[3-(3-chloro-2-methylphenyl)-thioureido]-acetamide, and 25.0 g of ethyl iodide. The hydrochloride salt was prepared in ethereal hydrogen chloride. Crystallization from ethyl acetate afforded the title compound as a white solid, monohydrochloride (5.1 g), m.p. 161-163° C. (dec.). Anal. Calcd. for. C12H13Cl N2O S . HCl: C, 47.22; H, 4.62; N, 9.18. Found: C, 47.03; H, 4.40; N, 9.09. Mass spectrum (+FAB, [M+H]+) m/z 269/271. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.05-9.85 (broad s, 2H), 7.62 (d, 1H), 7.39 (t, 1H), 7.33 (d, 1H), 4.48 (q, 2H), 3.20 (m, 2H), 2.15 (s, 3H), and 1.29 ppm (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-43a27572b4834c81b3dfac72cda48d97
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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