Triethylamine → N'-hydroxy-3-iodo-1-tosyl-1H-indole-5-carboximidamide

HRID 634274Notes

Reaction equation

HRID 634274 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:3]=1.CCN(CC)CC.[NH2:30][OH:31].Cl>CCO>[OH:31][N:30]=[C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:3]=[C:2]2[I:1])[NH2:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 219559133-iodo-1-tosyl-1H-indole-5-carbonitrile

Product 1

HCID 86725116N'-hydroxy-3-iodo-1-tosyl-1H-indole-5-carboximidamideYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-iodo-1-tosyl-1H-indole-5-carbonitrile (1 g, 2.37 mmol) in EtOH (10 mL) was added Et3N (1.65 mL, 11.87 mmol) followed by NH2OH.HCl (410 mg, 5.93 mmol) and the reaction was stirred for 48 h at RT. The solvent was removed in vacuo and the residue was treated with H2O (10 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (25 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The residue was further triturated with n-pentane to give N′-hydroxy-3-iodo-1-tosyl-1H-indole-5-carboximidamide (950 mg, 88.7%) as an off brown solid. MS (ESI, pos. ion) m/z: 455.8; 1H NMR (400 MHz, CDCl3): δ 7.99 (d, J=8.8 Hz, 1H), 7.84-7.73 (m, 4H), 7.68 (d, J=8.4 Hz, 1H), 7.63-7.61 (m, 1H), 7.31-7.24 (m, 1H), 4.92 (brs, 2H), 3.14-3.09 (m, 1H), 2.36 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with H2O (10 mL)
  3. extractionextracted with EtOAc (25 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (25 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was further triturated with n-pentane

Sources & evidence

ORD record
ord-d1dab56301694e7d8b28e31f0f1b3c59
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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