Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 732256

反応式

HRID 732256 の反応式
C1OC2C(=CSC=2)[O:3]C1CO.[CH:12]1([N:18]=[C:19]=[N:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(C1C=CC(C2C=CC(OCC(O)=O)=CC=2)=CC=1)#N>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:21]1([NH:20][C:19]([NH:18][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[O:3])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol2 回HCID 432431004-(Carboxymethyloxy)-4'-cyano-biphenyl

生成物 1

HCID 4277N,N'-Dicyclohexylurea

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

1.73 g of a mixture of 80% of EDT-methanol and 20% of hydroxy-PDT (corresponding to 8.08 mmol of EDT-methanol), 1.64 g of N,N′-dicyclohexyl-carbodiimide and 0.13 g of 4-(dimethylamino)pyridine are dissolved in 100 ml of CH2Cl2 and cooled to about 0° C. in an ice bath. 2.00 g of [(4′-cyano-1,1′-biphenyl-4-yl)oxy]acetic acid are added thereto a little at a time over a period of 1 hour while stirring and cooling in ice. The reaction is then continued at 23° C. for 42.5 hours. The N,N′-dicyclohexylurea formed is subsequently filtered off. The filtrate is washed in succession with 2×200 ml of 1 M HCl, 2×200 ml of saturated NaHCO3 solution and 2×200 ml of saturated NaCl solution. The organic phase is dried over MgSO4 and, after the magnesium sulphate has been filtered off, freed of solvent on a rotary evaporator. This gives 3.71 g of crude product which is purified by column chromatography using n-hexane/ethyl acetate 3:2. 0.39 g of the pure ester of EDT-methanol (I-a2) is obtained as colourless crystals.

後処理

  1. temperaturecooling in ice
  2. waitThe reaction is then continued at 23° C. for 42.5 hours

出典と根拠

ORDレコード
ord-d9cc4d9d1ea0421fa9c230a86bd71d7e
出典データセット
uspto-grants-2009_09
特許番号
US07585983B2

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