Sodium Carbonate → 7-bromo-2,3-dihydro-1,4-benzodioxin-6-amine

HRID 639013노트

반응식

HRID 639013 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Br:12]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.S(=O)(=O)(O)O>[Br:12][C:8]1[C:9]([NH2:11])=[CH:10][C:5]2[O:4][CH2:3][CH2:2][O:1][C:6]=2[CH:7]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 891481,4-Benzodioxan-6-ylamine

생성물 1

HCID 49832297-bromo-2,3-dihydro-1,4-benzodioxin-6-amine수율 115.6%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 2,3-dihydro-benzo[1,4]dioxin-6-ylamine (80 g, 530 mmol, 1 eq) in tetrahydrofuran (1000 mL) at −78° C. was treated with concentrated sulfuric acid (50 drops) then N-bromosuccinimide (94.2 g, 530 mmol, 1 eq) was added over 0.5 hour. After the addition the mixture was stirred at −78° C. for 1 hour then treated with solid sodium carbonate (12 g, 113 mmol, 0.21 eq). The mixture was evaporated and the residue partitioned between ether and water. The organic extract was dried, filtered and evaporated to give to oil that was chromatographed on silica gel eluting with dichloromethane to afford oil (141 g, 92%). LC/MS (ES) m/z 230 (MH+ 91%); 1H-NMR (400 MHz, d6-DMSO), 6.85 (1H, s, CHCNH2), 6.34 (1H, s, CHCBr), 4.79 (2H, s, NH2), 4.16 (4H, dd, J=16, 2×(CH2O))

후처리

  1. additionAfter the addition the mixture
  2. customThe mixture was evaporated
  3. customthe residue partitioned between ether and water
  4. extractionThe organic extract
  5. customwas dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give to oil that
  9. customwas chromatographed on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-5f69fbe819ab4a0f98d02cfe685acf79
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

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