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

HRID 2100517Notes

Reaction equation

HRID 2100517 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d03aef48d3a74206881e525b225c6450
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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