Iodoethane → HCID 44295791, compound

HRID 1417736Notes

Reaction equation

HRID 1417736 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

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 54277983HCID 54277983, compound

Product 1

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, mono-hydrochloride (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, 2 H), 7.62 (d, 1 H), 7.39 (t, 1 H), 7.33 (d, 1 H), 4.48 (q, 2 H), 3.20 (m, 2 H), 2.15 (s, 3 H), and 1.29 ppm (t, 3 H).

Workup

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

Sources & evidence

ORD record
ord-2c7d8eec810d4e9bab50f5728d6e8b75
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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