Water → HCID 21708644, compound

HRID 1599386Notes

Reaction equation

HRID 1599386 reaction equation
C(OC([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[C:8]([C:15]1[C:16]([Cl:20])=[N:17][S:18][N:19]=1)=[C:9]([Cl:14])[CH2:10]2)=O)C.[Cl-].[Cl-].[Cl-].[Al+3].O>C1(C)C=CC=CC=1>[Cl:14][C:9]1[CH2:10][CH:11]2[NH:6][CH:7]([CH2:13][CH2:12]2)[C:8]=1[C:15]1[C:16]([Cl:20])=[N:17][S:18][N:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 21708538HCID 21708538, compound

Product 1

HCID 21708644HCID 21708644, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-ethoxycarbonyl-3-chloro-2-(3-chloro-1,2,5-thiadiazol-4-yl)-8-azabicyclo[3.2.1]oct-2-ene (1.7 g, 5 mmol) (PCT/DK91/00236) in dry toluene (50 ml) was added aluminium trichloride (2.6 g, 20 mmol). The reaction mixture was heated to 80° C. and kept at this temperature for 10 min. After cooling water was carefully added to the reaction mixture. The water solution was extracted with methylene chloride (2×50 ml), then made basic with 4N sodiumhydroxide solution. The alkaline solution was extracted with diethylether (3×100 ml). The organic extracts from the basic extractions were dried over magnesium sulfate and evaporated. The residue was crystallized as the oxalate salt from acetone in 1.60 g yield.

Workup

  1. additionwas carefully added to the reaction mixture
  2. extractionThe water solution was extracted with methylene chloride (2×50 ml)
  3. extractionThe alkaline solution was extracted with diethylether (3×100 ml)
  4. extractionThe organic extracts from the basic extractions
  5. dry with materialwere dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was crystallized as the oxalate salt from acetone in 1.60 g
  8. customyield

Sources & evidence

ORD record
ord-5a45fd0b931246859f19a8b210346fd6
Source dataset
uspto-grants-1998_04
Patent number
US05741788

Reaction notes

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