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

HRID 1870770Notes

Reaction equation

HRID 1870770 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-cb7e2cfed299473985791b6c1cc2edde
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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