Methanol → 1,6-Hexanediyl dianthranilate

HRID 51199

반응식

HRID 51199 반응식
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14]C(=O)[O:12][C:10]2=O.[N:21]12[CH2:28][CH2:27]N(CC1)CC2.[CH3:29][OH:30]>CN(C)C=O.O>[C:29]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:8][C:10](=[O:12])[C:9]1[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:14])(=[O:30])[C:4]1[C:28](=[CH:27][CH:1]=[CH:2][CH:3]=1)[NH2:21]

참가 물질

7

반응물 4

HCID 887MethanolHCID 8359Isatoic AnhydrideHCID 9237DabcoHCID 123741,6-Hexanediol

생성물 1

HCID 865907771,6-Hexanediyl dianthranilate수율 78%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of 1,6-hexanediol (118 grams, 1.0 mol; obtained from Sigma-Aldrich), isatoic anhydride (367 grams, 2.25 mol), and 1,4-diazabicyclo[2.2.2]octane (22.4 grams, 0.20 mol) in 500 milliliters of dimethyl formamide in a 4 liter beaker was heated at 120° C. for 1.5 hours. The mixture was then cooled to room temperature and was stirred as first methanol (1,500 milliliters) and then water (750 milliliters) were added. The resultant suspension was stirred for 2 hours, and then was filtered. The solid was washed in the filter funnel with 2×200 milliliter portions of 75:25 methanol/water, then with 250 milliliters of water, and again with 2×200 milliliter portions of 75:25 methanol/water. Drying in the air for 72 hours gave the desired 1,6-hexanediyl dianthranilate product as a light beige solid (277.5 grams, 78 percent yield). A 1H-NMR spectrum indicated that the product was highly pure (greater than 98 percent). The melting point of this product as measured by Differential Scanning Calorimetry was 78° C.

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationwas filtered
  3. washThe solid was washed in the filter funnel with 2×200 milliliter portions of 75:25 methanol/water
  4. customDrying in the air for 72 hours

출처 및 근거

ORD 기록
ord-963bed18cac149169ca1c9bf22997171
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713614B2

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