Hydrochloric Acid → Methyl 4-(4,4-dimethyl-2-oxo-imidazolidin-1-yl)-3-methyl-benzoate

HRID 1629883ノート

反応式

HRID 1629883 の反応式
[CH3:1][C:2]([NH:6][C:7](=[O:20])[NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH3:19])([CH3:5])[CH2:3]O.[K].CC(C)([O-])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C1COCC1.O>[CH3:1][C:2]1([CH3:5])[CH2:3][N:8]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[CH3:19])[C:7](=[O:20])[NH:6]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 50987170Potassium tertbutoxideHCID 67048374Methyl 4-(3-[1,1-dimethyl-2-hydroxy-ethyl]ureido)-3-methyl-benzoate

生成物 1

HCID 67048320Methyl 4-(4,4-dimethyl-2-oxo-imidazolidin-1-yl)-3-methyl-benzoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

7.00 g (25.0 mmol) methyl 4-(3-[1,1-dimethyl-2-hydroxy-ethyl]-ureido)-3-methyl-benzoate are dissolved in 400 ml THF at 0° C. and combined with 6.73 g (60.0 mmol) potassium-tert.-butoxide. After stirring for 15 minutes at 0° C. a solution of 5.72 g (30.0 mmol) p-toluenesulphonic acid in 50 ml THF is added dropwise. After another 10 minutes stirring at 0° C. 300 ml of water are added, the mixture is neutralised with 1-molar hydrochloric acid and the THF is removed i. vac. The residue is extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down i. vac. Then the residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol=100:0->97:3).

後処理

  1. additionis added dropwise
  2. customthe THF is removed i
  3. extractionThe residue is extracted with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated down i
  6. customThen the residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol=100:0->97:3)

出典と根拠

ORDレコード
ord-33c994f3a98e448b95abf23dcf0a15be
出典データセット
uspto-grants-2014_07
特許番号
US08791103B2

反応ノート

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