Sulfuric Acid → HCID 15007755, compound

HRID 847370Notes

Reaction equation

HRID 847370 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][C:6]=1[F:20])[CH2:3][OH:4].[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=1[C:24](O)=O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=1[C:24]1[O:4][CH2:3][CH:2]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][C:6]=2[F:20])[N:1]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 97962,6-Difluorobenzoic acidHCID 15007754HCID 15007754, compound

Product 1

HCID 15007755HCID 15007755, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2.81 g (10 millimoles) of 2-amino-2-(2-fluoro-4-n-nonylphenyl)ethanol, 1.77 g (10 millimoles) of 2,6-difluorobenzoic acid and 20 ml of toluene, 3 g (30 millimoles) of concentrated sulfuric acid was added and refluxed for 7 hours with stirring. After cooling again to room temperature, the reaction mixture was washed successively with 30 ml of a 10% aqueous sodium hydroxide solution and then 30 ml of a saturated sodium chloride solution, desiccated over anhydrous sodium sulfate and concentrated under reduced pressure. This concentrate was purified by silica-gel column chromatography using a 8/2 solvent mixture of n-hexane/ethyl acetate to obtain 2-(2,6-difluorophenyl)-4-(2-fluoro-4-n-nonylphenyl)-2-oxazoline (Compound Number 42).

Workup

  1. additionwas added
  2. temperaturerefluxed for 7 hours
  3. washthe reaction mixture was washed successively with 30 ml of a 10% aqueous sodium hydroxide solution
  4. concentrationconcentrated under reduced pressure
  5. customThis concentrate was purified by silica-gel column chromatography
  6. additiona 8/2 solvent mixture of n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-0fead3fa4f4b49098ec24122560b7e99
Source dataset
uspto-grants-1992_08
Patent number
US05141948

Reaction notes

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