Sodium Carbonate → HCID 12811241, compound

HRID 235943Notes

Reaction equation

HRID 235943 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=2)=[CH:5][CH:4]=1.[Br:18]Br.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:18][C:11]1[N:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:13][C:12]=1[C:14]([F:17])([F:15])[F:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 178488961HCID 178488961, compound

Product 1

HCID 12811241HCID 12811241, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 7 (5 g, 0.025 mol) in CHCl3 (200 ml) was added dropwise a solution of Br2 (1.3 mol, d=3.1, 4.0 g, 0.25 mol) in 100 ml CHCl3. After the addition, the solution was stirred at room temperature for 5 h, poured onto saturated Na2CO3 solution, and separated. The aqueous layer was extracted with CHCl3 (3×). The organic layers were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with CHCl3 to yield 4.4 g (65%) of 8. An analytical sample was prepared by crystallization from petroleum ether-CHCl3, m.p. 177°-178° C.

Workup

  1. additionAfter the addition
  2. customseparated
  3. extractionThe aqueous layer was extracted with CHCl3 (3×)
  4. customThe organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica gel
  8. washthe product eluted with CHCl3

Sources & evidence

ORD record
ord-2347b57b446a4aff8e375152580026e9
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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