Iodoethane → HCID 59580870, compound

HRID 1470428Notes

Reaction equation

HRID 1470428 reaction equation
[CH2:1]([NH:3][C:4](=[S:19])[N:5]([CH3:18])[C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:17])[CH3:2].I[CH2:21][CH3:22]>C(O)C>[CH2:21]([S:19][C:4](=[N:3][CH2:1][CH3:2])[N:5]([CH3:18])[C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:17])[CH3:22]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 59580664HCID 59580664, compound

Product 1

HCID 59580870HCID 59580870, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-ethyl-1-methyl-1-(4-methyl-2-(pyridin-3-yl)thiazol-5-yl)thiourea (70 mg, 0.239 mmol) and iodoethane (74.7 mg, 0.479 mmol) in ethanol (5 mL) was heated at 80° C. for 6 h in a sealed tube. Upon cooling the solvent was removed under reduced pressure and the residue purified via silica gel chromatography (0 to 100% ethyl acetate/hexanes) to furnish the title compound as a clear oil (30 mg, 39%): 1H NMR (400 MHz, CDCl3) δ 9.10 (d, J=2.0 Hz, 1H), 8.64 (dd, J=4.6 Hz, 1.4 Hz, 1H), 8.20 (d, J=4.2 Hz, 1H), 7.41-7.37 (m, 1H), 3.63 (q, J=7.6 Hz, 2H), 3.22 (s, 3H), 2.72 (q, J=7.8 Hz, 2H), 2.38 (s, 3H), 1.28-1.17 (m, 6H); ESIMS m/z 321 (M+1).

Workup

  1. temperatureUpon cooling the solvent
  2. customwas removed under reduced pressure
  3. customthe residue purified via silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-49921c00c52a47718b00ca8bf46bd148
Source dataset
uspto-grants-2015_04
Patent number
US09006446B2

Reaction notes

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