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Iodoethane → HCID 136383528, compound

HRID 732933
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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)
  • additiona mixture of CHCl3:MeOH (9:1) as the eluant
  • Sources & evidence

    ORD record
    ord-f59584068488417b915d24ae6a066db5
    Source dataset
    uspto-grants-2009_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US07589086B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes