Sodium Carbonate → 3-(9-hydroxynonyl)-2H-1,3-benzoxazine-2,4(3H)-dione

HRID 553262

반응식

HRID 553262 반응식
[CH:1]1[CH:2]=[CH:3][C:4]2[O:12][C:10](=[O:11])[NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CCCCCCC>CN(C)C(=O)C>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:9]1[C:7](=[O:8])[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[O:12][C:10]1=[O:11]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 162582H-1,3-Benzoxazine-2,4(3H)-dioneHCID 1087001-Nonanol, 9-bromo-HCID 21899848Ethylacetate heptane

생성물 1

HCID 219084243-(9-hydroxynonyl)-2H-1,3-benzoxazine-2,4(3H)-dione수율 80.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
77.5 °C

실험 절차

A mixture of 6.525 g (40 mmol) of carsalam, 10.26 g (44 mmol) of 9-bromo-1-nonanol, and 5.30 g (50 mmol) of sodium carbonate in 30 mL N,N-dimethylacetamide (DMA) was heated at 75-80° C. for 3 hours. TLC (eluent: ethyl acetate/heptane) indicated the reaction was completed. The reaction was carefully poured into a mixture of ice-water. The resulting white solid was stirred for 1 hour. It was collected on sintered glass funnel, washed with water, hexane and dried in vacuo to yield 9.80 g of 3-(9-hydroxynonyl)-2H-1,3-benzoxazine-2,4(3H)-dione (80%). To a slurry of 6.11 g (20 mmol) of 3-(9-hydroxynonyl)-2H-1,3-benzoxazine-2,4(3H)-dione in 10 mL of N,N-dimethylacetamide at room temperature was added 20.4 mL (20.4 mmol) of potassium t-butoxide in THF solution. The clear brown solution became very thick. More DMA (10 mL) was added, and the mixture was heated at reflux for 5 minutes. 0.664 g (4 mmol) of potassium iodide was added, followed by dropwise addition of 3.34 (20 mmol) of ethyl bromoacetate. The reaction was refluxed for 1 hour, cooled to about 35° C. and poured into ice-water. A gum resulted. The supernatant liquid was decanted and fresh water was added. That procedure was repeated twice. The gum was dissolved in THF. The THF solution was carefully poured into hexane. The resulting solid was collected, washed with hexane and dried in vacuo. The weight of the desired product was 2.36 g (35%). HPLC: 4.39 min.; Mp: 125-128° C. HNMR (M DSO d6): δ 1.25 (12H, m), 1.37 (2H, m), 1.53 (2H, m), 3.28 (2H, m), 3.36 (2H, t), 4.85 (2H, s), 7.07 (2H, m), 7.45 (1H, t), 7.88 (1H, d), 8.70 (1H, t). Anal. Calcd for C18H27NO6: C, 64.07; H, 8.07; N, 4.15. Found: C, 63.71; H, 8.29; N, 4.31.

후처리

  1. customIt was collected on sintered glass funnel
  2. washwashed with water, hexane
  3. customdried in vacuo

출처 및 근거

ORD 기록
ord-ede4f829176f4391803857c18f6095f1
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951971B1

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