N,N-二甲基甲酰胺 → N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide

HRID 36062笔记

反应方程式

HRID 36062 反应方程式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[CH2:8][C:7]=2[CH:15]=1)#[N:2].[CH3:16][N:17]=[C:18]=[S:19].CN(C)C=O.CC(C)([O-])C.[K+]>C(O)(=O)C>[CH3:16][NH:17][C:18]([C:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[C:9]=1[OH:14])=[S:19]

参与物

6

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 11167异硫氰酸甲酯HCID 148695546-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-oneHCID 23665647叔丁醇钾

产物 1

HCID 135720096N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide收率 68.5%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

To a mixture of 1.5 g of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-one, 0.6 g of methyl isothio-cyanate, and 15 ml of dried N,N-dimethylformamide was added 0.93 g of potassium t-butoxide with stirring under ice-cooling, followed by stirring for 4 hours under ice-cooling. Ice-water was added to the reaction mixture, and the mixture was made acidic with acetic acid and then extracted with diethyl ether. The ether layer was washed with water and dried over sodium sulfate. The ether layer was removed by distillation, and the residue was recrystallized from ethanol to yield 1.4 g of N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide represented by formula shown below.

后处理

  1. temperaturecooling
  2. stirringby stirring for 4 hours under ice-
  3. temperaturecooling
  4. extractionextracted with diethyl ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe ether layer was removed by distillation
  8. customthe residue was recrystallized from ethanol

来源与证据

ORD记录
ord-de48dd21366944da9ff0804dea9a9368
来源数据集
uspto-grants-1995_05
专利号
US05412117

反应笔记

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