Sodium Carbonate → HCID 12811241, compound

HRID 1721994Notes

Reaction equation

HRID 1721994 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 x). 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 x)
  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-821071ce2e574b6183255db2b478ba21
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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