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

HRID 2100517

반응식

HRID 2100517 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d03aef48d3a74206881e525b225c6450
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572801B2

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