Sodium Carbonate → HCID 86737884, compound

HRID 848214Notes

Reaction equation

HRID 848214 reaction equation
[F:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[Cl:13][C:14]1[C:19]([NH2:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1.CO[CH:27]1[CH2:31][CH2:30][CH:29](OC)O1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[F:1][C:2]1[C:7]([N:8]2[CH:19]=[CH:18][CH:17]=[CH:16]2)=[CH:6][C:5]([C:9]([F:10])([F:11])[F:12])=[CH:4][N:3]=1.[Cl:13][C:14]1[C:19]([N:20]2[CH:27]=[CH:31][CH:30]=[CH:29]2)=[CH:18][C:17]([C:21]([F:22])([F:23])[F:24])=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 790982,5-DimethoxytetrahydrofuranHCID 86737885HCID 86737885, compound

Product 1

HCID 86737884HCID 86737884, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the mixture (1.1 g) from Example 17 b., 2,5-dimethoxytetrahydrofuran (0.9 g, 0.007 m) and acetic acid (5 ml) was heated at reflux with stirring. After 11/2 hours, the solution was cooled and poured into saturated Na2CO3 solution. The aqueous layer was extracted with CHCl3 and the organic layer was dried over Na2SO4, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 1:1 CH2Cl2 :hexane to yield 0.65 g of a mixture of 2-chloro and 2-fluoro-3-(1-pyrrolyl)-5-trifluoromethylpyridine.

Workup

  1. temperatureat reflux
  2. temperatureAfter 11/2 hours, the solution was cooled
  3. extractionThe aqueous layer was extracted with CHCl3
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica gel
  8. washthe product eluted with 1:1 CH2Cl2

Sources & evidence

ORD record
ord-2ce5454eb25b44f0b94306ddf8e59aa9
Source dataset
uspto-grants-1981_10
Patent number
US04294969

Reaction notes

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