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

HRID 551237笔记

反应方程式

HRID 551237 反应方程式
[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

参与物

7

反应物 4

HCID 313盐酸HCID 6101对甲苯磺酸HCID 50987170Potassium tertbutoxideHCID 67048374Methyl 4-(3-[1,1-dimethyl-2-hydroxy-ethyl]ureido)-3-methyl-benzoate

产物 1

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

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂2 次

反应条件

温度
0 °C

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-f90eaa8af99c495393e006238c018a69
来源数据集
uspto-grants-2011_05
专利号
US07947700B2

反应笔记

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