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

HRID 2100517

反応式

HRID 2100517 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d03aef48d3a74206881e525b225c6450
出典データセット
uspto-grants-2009_08
特許番号
US07572801B2

関連ノート

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