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HRID485633

反应详情

EQUATION

反应方程式

HRID 485633 的结构方程式

REACTANTS

反应物

4
结构：O=C(O)CCCc1ccc(N(CCCl)CCCl)cc1
HCID2708

Chlorambucil

C14H19Cl2NO2

结构：C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
HCID5755

Prednisolone

C21H28O5

结构：Cc1ccc(S(=O)(=O)O)cc1
HCID6101

4-Methylbenzenesulfonic acid

C7H8O3S

结构：C(=NC1CCCCC1)=NC1CCCCC1
HCID10868

Dicyclohexylcarbodiimide

C13H22N2

PRODUCTS

生成物

1
结构：C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)COC(=O)CCCc1ccc(N(CCCl)CCCl)cc1
HCID34457

Prednimustine

C35H45Cl2NO6

收率 91%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：CC(=O)O
溶剂HCID176

Acetic Acid

C2H4O2

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

To 250 ml CH2Cl2 is added with stirring 36 g prednisolone (0.10 mol), 31.3 g chlorambucil (0,103 mol), 1.2 g DMAP (0,01 mol) and 1.1 g pTSA (0,06 mol). The reaction mixture is cooled to 0° C. and with continued stirring at this temperature a solution of 22.7 g DCC (0,11 mol) in 50 ml CH2Cl2 is slowly added. The reaction mixture is then kept at 0° C. with stirring for 20 h. 3 ml acetic acid is added and precipitated urea filtered off. The filtrate is evaporated in vacuo and the residue recrystallized from ethanol to give 58.9 g of TLC pure prednimustine (91% yield) without any discolouration. M.P. 165°-166° C.

WORKUP

后处理

  1. additionis slowly added
  2. customis then kept at 0° C.
  3. customprecipitated urea
  4. filtrationfiltered off
  5. customThe filtrate is evaporated in vacuo
  6. customthe residue recrystallized from ethanol