Methanol → 4,4'-Bicyclohexanediyl dianthranilate

HRID 51197

反応式

HRID 51197 の反応式
[CH:1]1([OH:13])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[C:14]12[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH:19]C(=O)[O:17][C:15]2=[O:16].[N:26]12[CH2:33][CH2:32]N(CC1)CC2.[CH3:34][OH:35]>CN(C)C=O>[C:34]([O:13][CH:1]1[CH2:2][CH2:3][CH:4]([CH:7]2[CH2:12][CH2:11][CH:10]([O:17][C:15](=[O:16])[C:14]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH2:19])[CH2:9][CH2:8]2)[CH2:5][CH2:6]1)(=[O:35])[C:3]1[C:33](=[CH:32][CH:6]=[CH:1][CH:2]=1)[NH2:26]

参加物

6

反応物 4

HCID 887MethanolHCID 8359Isatoic AnhydrideHCID 9237DabcoHCID 755184-Cyclohexylcyclohexanol

生成物 1

HCID 865907754,4'-Bicyclohexanediyl dianthranilate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
120 °C

実験手順

A mixture of 4,4′-bicyclohexanol (49.5 grams, 0.25 mol; obtained from Sigma-Aldrich), isatoic anhydride (122 grams, 0.75 mol), and 1,4-diazabicyclo[2.2.2]octane (66.0 grams, 0.50 mol) in 200 milliliters of dimethyl formamide was stirred at 120° C. for 1 hour, then was cooled to about 80° C. The solution was then treated first with dimethyl formamide (100 milliliters) and then with methanol (900 milliliters). The resultant suspension was stirred for 2 hours, and then was filtered. The solid was washed with 4×100 milliliter portions of methanol and was dried at 60° C. for 20 hours. The 4,4′-bicyclohexanediyl dianthranilate product was obtained as a cream solid (58.2 grams, 53 percent yield) which was adjudged by 1H-NMR spectroscopy to be pure (greater than 98 percent). The melting point of this product as measured by Differential Scanning Calorimetry was 236° C.

後処理

  1. temperaturewas cooled to about 80° C
  2. filtrationwas filtered
  3. washThe solid was washed with 4×100 milliliter portions of methanol
  4. customwas dried at 60° C. for 20 hours

出典と根拠

ORDレコード
ord-b3f83f9efd8e479bb3db950b46f6c8db
出典データセット
uspto-grants-2004_03
特許番号
US06713614B2

関連ノート

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