Iodoethane → HCID 136383528, compound

HRID 732933Notes

Reaction equation

HRID 732933 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([S:14][CH3:15])[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1.[CH2:22](I)C>>[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([S:14][CH2:15][CH3:22])[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 135741846HCID 135741846, compound

Product 1

HCID 136383528HCID 136383528, compoundYield 65%

Procedure

Compound 8b was prepared according to the synthetic sequence described for compound 8a, by using ethyl iodide as alkylating agent. In this case, the crude was purified by column chromatography (Silica Gel, 100 Mesh) using a mixture of CHCl3:MeOH (9:1) as the eluant, to afford the pure product 8b (2.05 g, 65%) as a light yellow solid: mp 199-200° C. 1H NMR: δ 1.45 (t, J=7.6, 3H, CH3), 3.22 (q, J=7.4, 2H, CH2), 4.44-4.68 (m, 2H, CH2N), 5.21-5.30 (m, 1H, CHO), 7.26-7.47 (m, 5H Ar), 8.10 (s, 1H, H-3). IR cm−1 3470 (NH), 3450-3340 (OH), 1670 (CO). Anal. (C15H16N4O2S) C, H, N, S.

Workup

  1. customCompound 8b was prepared
  2. customIn this case, the crude was purified by column chromatography (Silica Gel, 100 Mesh)
  3. additiona mixture of CHCl3:MeOH (9:1) as the eluant

Sources & evidence

ORD record
ord-f59584068488417b915d24ae6a066db5
Source dataset
uspto-grants-2009_09
Patent number
US07589086B2

Reaction notes

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