Diethyl Ether → 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide

HRID 1870770노트

반응식

HRID 1870770 반응식
C([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][N:12]([C:15]1[N:20]=[N:19][C:18]([C:21]([NH2:23])=[O:22])=[CH:17][CH:16]=1)[CH2:13][CH3:14])C1C=CC=CC=1.CSC.B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)C>ClCCl.CO>[Br:28][C:25]1[CH:26]=[CH:27][C:9]([OH:8])=[C:10]([CH:24]=1)[CH2:11][N:12]([C:15]1[N:20]=[N:19][C:18]([C:21]([NH2:23])=[O:22])=[CH:17][CH:16]=1)[CH2:13][CH3:14]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 10899259Boron trichloride methyl sulfideHCID 186932216-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide

생성물 1

HCID 186932416-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide수율 52.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매3회

실험 절차

6-[N-(2-Benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxamide (3.24 g, 7.3 mmol) in dichloromethane (50 ml) was treated with boron trichloride dimethyl sulphide reagent (18.5 ml, 2M solution) in dichloromethane (37 mmol) and the solution stirred at ambient temperature for 6 days. The mixture was carefully treated with excess aqueous sodium bicarbonate solution to give a pH of around 9. Dichloromethane was added, the organic and aqueous layers separated and the aqueous layer washed with dichloromethane. The combined organic extracts were then washed with brine, dried and evaporated to give a sticky solid. This was treated with diethylether (30 ml) and methanol (3 ml) and left at ambient temperature overnight. The resultant solid was filtered, washed with diethylether and sucked dry to give 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide (1.34 g, 52%).

후처리

  1. customto give a pH of around 9
  2. customthe organic and aqueous layers separated
  3. washthe aqueous layer washed with dichloromethane
  4. washThe combined organic extracts were then washed with brine
  5. customdried
  6. customevaporated
  7. customto give a sticky solid
  8. waitleft at ambient temperature overnight
  9. filtrationThe resultant solid was filtered
  10. washwashed with diethylether
  11. customsucked dry

출처 및 근거

ORD 기록
ord-cb7e2cfed299473985791b6c1cc2edde
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100258

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