Ethanol → HCID 178480159, compound

HRID 1668455Notes

Reaction equation

HRID 1668455 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][NH2:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.C(O)C.I.CS[C:26]([C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)=[NH:27]>C(OCC)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][NH:19][C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[NH:27])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

5

Reactant 3

HCID 702EthanolHCID 59004652HCID 59004652, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480159HCID 178480159, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 36 (124 mg, 0.482 mmol) and anhydrous ethanol (10 mL) were charged to a dry argon purged flask fitted with magnetic stirbar. Thiophene-2-carboximidothioic acid methyl ester hydroiodide (178.5 mg, 0.626 mmol) is added to the flask and the reaction was stirred under argon at ambient temperature for 96 hours. The solution was diluted with diethyl ether (50 mL) resulting in the formation of an off-white precipitate which was collected on a sintered glass funnel and washed with ether. The solid was partitioned between H2O and ethyl acetate and 3M sodium hydroxide solution added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (2M NH3 in methanol:CH2Cl2, 1:9) to afford a pale yellow residue 37 (100 mg, 56.6%); 1H NMR (DMSO-d6) δ 7.60 (d, 1H, J=3.8 Hz), 7.51 (m, 2H), 7.39-7.34 (2×m, 2H), 7.16-7.13 (m, 1H), 7.06 (dd, 1H, J=3.8, 5.1 Hz), 6.86-6.54 (brs, 2H), 6.37 (d, 1H, J=3.0 Hz), 4.38 (s, 2H), 4.16 (t, 2H, J=7.3 Hz), 2.94-2.87 (m, 1H), 2.16 (s, 3H), 2.11-1.92 (2×m, 3H), 1.89-1.80 (m, 1H), 1.69-1.55 (m, 3H), 1.48-1.36 (m, 1H); ESI-MS (m/z, %): 367 (M+1, 100%).

Workup

  1. customfitted with magnetic stirbar
  2. customresulting in the formation of an off-white precipitate which
  3. customwas collected on a sintered glass funnel
  4. washwashed with ether
  5. customThe solid was partitioned between H2O and ethyl acetate and 3M sodium hydroxide solution
  6. additionadded
  7. customThe mixture was transferred to a separatory funnel
  8. customthe organic layer collected
  9. extractionThe aqueous layer was further extracted with ethyl acetate
  10. washthe combined organic layers were washed with brine
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customthe residue purified via chromatography on silica gel (2M NH3 in methanol:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-9e5d7f022332464587506fb4f759ba1d
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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