Dimethylformamide → 1,10-Decanediyl dianthranilate

HRID 1369136ノート

反応式

HRID 1369136 の反応式
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[C:13]12[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:18]C(=O)[O:16][C:14]2=O.[N:25]12[CH2:32][CH2:31]N(CC1)CC2.CN(C)[CH:35]=[O:36]>O.CO>[C:35]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:14](=[O:16])[C:13]1[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:18])(=[O:36])[C:4]1[C:32](=[CH:31][CH:1]=[CH:2][CH:3]=1)[NH2:25]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8359Isatoic AnhydrideHCID 9237DabcoHCID 371531,10-Decanediol

生成物 1

HCID 865907761,10-Decanediyl dianthranilate収率 29%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

1,10-Decanediol (174 grams, 1.0 mol), isatoic anhydride (367 g, 2.25 mol; obtained from Sigma-Aldrich), 1,4-diazabicyclo[2.2.2]octane (22.4 grams, 0.20 mol), and dimethyl formamide (500 milliliters) were combined in 2 liter beaker and the resulting mixture was heated at 120° C. for 1 hour. The mixture was then cooled to room temperature and was treated first with methanol (1,500 milliliters) and then with water (500 milliliters). The solution turned cloudy, and then formed crystals. The crystal suspension was stirred for 2 hours at room temperature, and then was filtered. The solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water, and then was dried to give 1,10-decanediyl dianthranilate as a light beige solid (119 grams, 29 percent yield). The product was adjudged to be highly pure (greater than 98 percent) by 1H-NMR1 The melting point of this product as measured by Differential Scanning Calorimetry was 77° C.

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. customformed crystals
  3. filtrationwas filtered
  4. washThe solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water
  5. customwas dried

出典と根拠

ORDレコード
ord-6cad3cc8fe004ee0ac96b1ad469b57cd
出典データセット
uspto-grants-2003_06
特許番号
US06576748B1

反応ノート

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