Methyl iodide → HCID 178489504、化合物

HRID 929663ノート

反応式

HRID 929663 の反応式
CI.[Br:3][C:4]1[N:9]=[C:8]([NH:10][C:11]([NH2:13])=S)[CH:7]=[CH:6][CH:5]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].ClCCl.CCCCC>CO.C(O)C>[Br:3][C:4]1[N:9]=[C:8]([NH:10][C:11]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[O:15][CH3:14])=[NH:13])[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 812922-MethoxybenzylamineHCID 21877063Dichloromethane pentaneHCID 22170428(6-Bromo-pyridin-2-YL)thiourea

生成物 1

HCID 178489504HCID 178489504、化合物収率 75.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒2 回

実験手順

0.87 mL (1384 mmol) methyl iodide diluted in 2 mL methanol was added dropwise to 2.00 g (8.65 mmol) N-(6-bromopyridin-2-yl)thiourea suspended in 30 mL methanol, and the mixture was heated for 1.45 hr under reflux. The reaction mixture was in solution. The methylated intermediate product, consisting of methyl N-(6-bromopyridin-2-yl)imidothiocarbamate hydroiodide (ESI-MS [M+H+]=247.85 calculated for C7H8BrN3S=246), was freed of solvent under vacuum. The intermediate product was then suspended in 25 mL ethanol, and after addition of 2.37 mL (18.168 mmol) 2-methoxybenzylamine was heated for 3 hr under reflux, whereupon the solid completely dissolved. For workup the solvent was removed under vacuum, and the crude mixture was taken up in dichloromethane. Extraction was performed with water (2×100 mL) and with 2 N sodium hydroxide solution (1×100 mL) to liberate the iodide salt. Subsequent washing of the organic phase with water (1×100 mL), drying over magnesium sulfate, and evaporation of the solvent under vacuum resulted in a light brown-yellow oil, from which a colorless crystallizate was isolated from dichloromethane/pentane in a refrigerator at 5° C. Further fractionated crystallization in acetonitrile/water resulted in a total of 2.18 g (6.50 mmol, 75%) N-(6-bromopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine.

後処理

  1. temperaturethe mixture was heated for 1.45 hr
  2. temperatureunder reflux
  3. temperaturewas heated for 3 hr
  4. temperatureunder reflux, whereupon the solid
  5. dissolutioncompletely dissolved
  6. customFor workup the solvent was removed under vacuum
  7. extractionExtraction
  8. washSubsequent washing of the organic phase with water (1×100 mL)
  9. dry with materialdrying over magnesium sulfate, and evaporation of the solvent under vacuum
  10. customresulted in a light brown-yellow oil, from which a colorless crystallizate
  11. customcrystallization in acetonitrile/water

出典と根拠

ORDレコード
ord-1668c1bbbce54d109783d16e522d6d53
出典データセット
uspto-grants-2016_03
特許番号
US09296697B2

反応ノート

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