Triethylamine → HCID 58316723, compound

HRID 2042179Notes

Reaction equation

HRID 2042179 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=S)[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.CCN(CC)CC.Cl.[NH2:23][OH:24]>CCO.O>[OH:24][NH:23][C:9](=[N:8][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]=1)[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58316709HCID 58316709, compound

Product 1

HCID 58316723HCID 58316723, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-(5-Iodo-pyridin-2-yl)-2,2-dimethyl-thiopropionamide (example 39, step 2) (5.1 g, 15.9 mmol) was dissolved in 50 ml of EtOH and Et3N (2.9 ml, 20.7 mmol, 1.3 equiv.) and hydroxylamine hydrochloride (1.3 g, 19.1 mmol, 1.2 equiv.) were added at room temperature. The mixture was stirred for 2 hours at room temperature. The suspension was diluted with 100 ml of water and filtered. The crystals were washed with water and dried for 2 hours at 50° C. and <10 mbar. The desired N-hydroxy-N′-(5-iodo-pyridin-2-yl)-2,2-dimethyl-propionamidine (4.35 g, 86% yield) was obtained as a white solid, MS: m/e=319.9 (M+H+).

Workup

  1. filtrationfiltered
  2. washThe crystals were washed with water
  3. customdried for 2 hours at 50° C.

Sources & evidence

ORD record
ord-a6017a2ef67b4d098d3a9f8f0a5fb605
Source dataset
uspto-grants-2013_11
Patent number
US08586581B2

Reaction notes

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