Hydrochloric Acid → 6-(2-(4-(4-Quinazolinyl)piperazinyl)ethyl)-benzoxazolone

HRID 1639267노트

반응식

HRID 1639267 반응식
Br[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1.[N:14]1([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.[I-].[Na+].C(O)C>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]([N:14]2[CH2:15][CH2:16][N:17]([CH2:2][CH2:3][C:4]3[CH:13]=[CH:12][C:7]4[NH:8][C:9](=[O:11])[O:10][C:6]=4[CH:5]=3)[CH2:18][CH2:19]2)=[N:21][CH:22]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 18585334-Piperazin-1-ylquinazolineHCID 133060876-Bromoethylbenzoxazolone

생성물 1

HCID 145814566-(2-(4-(4-Quinazolinyl)piperazinyl)ethyl)-benzoxazolone수율 68.6%

시약·촉매·용매 3

HCID 5238Sodium Iodide촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.22 g (5.05 mmol) of 6-bromoethylbenzoxazolone, 1.08 g (5.05 mmol) of 4-piperazinylquinazoline, 0.85 g (8.0 mmol) of sodium carbonate, 2 mg of sodium iodide, and 35 ml of ethanol. The reaction was refluxed for 3 days, cooled, diluted with water, and the pH adjusted to 4 with 1N HCl. The aqueous layer was separated, the pH adjusted to 7 with 1N NaOH, and the product extracted into ethyl acetate. The ethyl acetate layer was washed with brine, dried, and evaporated to give 1.3 g of a yellow oil. The oil was crystallized form chloroform (1.1 g), dissolved in ethyl acetate, ethyl acetate saturated with HCl gas added, and the mixture concentrated to dryness. The residue gave 0.9 g (58%) of a yellow salt, m.p. 200° C. NMR (d, CDCl3): 2.72 (m, 6H), 2.86 (m, 2H), 3.83 (m, 4H), 6.9-7.9 (m, 7H), 8.72 (s, 1H).

후처리

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed for 3 days
  3. temperaturecooled
  4. customThe aqueous layer was separated
  5. extractionthe product extracted into ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. customdried
  8. customevaporated

출처 및 근거

ORD 기록
ord-f55d286bd08541df92d040d5c209a64d
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883795

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