Triethylamine → methyl N-(2,5-dichloropyridine-3-carbonyl)carbamimidothioate

HRID 2100517

Reaktionsgleichung

Reaktionsgleichung von HRID 2100517
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.I.[NH2:13][C:14]([S:16][CH3:17])=[NH:15].C(N(CC)CC)C>C(Cl)(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]([NH:15][C:14](=[NH:13])[S:16][CH3:17])=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 197812S-methylthiouronium iodideHCID 27999962,5-Dichloro-nicotinoyl chloride

Produkt 1

HCID 140520075methyl N-(2,5-dichloropyridine-3-carbonyl)carbamimidothioateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under an atmosphere of nitrogen, and at a temperature of 0° C., a solution of 2,5-dichloropyridine-3-carbonyl chloride [175277-81-3] (4.82 g, 23 mmol) in CHCl3 (7 ml) was slowly added to a solution of methyl aminomethanimidothioate hydroiodide [4338-95-8] (5.00 g, 23 mmol) and triethylamine (6.36 ml, 46 mmol) in pyridine (7 ml). The reaction mixture was stirred at r.t. over the weekend, was taken up in ethyl acetate and washed (water). After drying (Na2SO4) and evaporation of the solvent, the residue was purified (column chromatography, silica gel, CH2Cl2/MeOH) to give 1-(2,5-dichloro-pyridine-3-carbonyl)-2-methyl-isothiourea (3.50 g, 13 mmol; 58%). MS: m/e=262.0 [M+H+]); 1H NMR (d6-DMSO): δ 2.44 (s, 3H), 8.27 (d, 1H), 8.55 (d, 1H), 9.15 (bs, 1H), 9.55 (bs, 1H).

Aufarbeitung

  1. washwashed (water)
  2. customAfter drying
  3. custom(Na2SO4) and evaporation of the solvent
  4. customthe residue was purified (column chromatography, silica gel, CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-d03aef48d3a74206881e525b225c6450
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572801B2

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