Triethylamine → HCID 19888147, compound

HRID 654044Notes

Reaction equation

HRID 654044 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][NH:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([NH2:13])[C:7]=1[OH:14].C(N(CC)CC)C.[C:25]([O:28][CH2:29][C:30](Cl)=[O:31])(=[O:27])[CH3:26]>C1COCC1>[F:17][C:2]([F:1])([F:16])[CH2:3][NH:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([NH:13][C:30](=[O:31])[CH2:29][O:28][C:25](=[O:27])[CH3:26])[C:7]=1[OH:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 19888152HCID 19888152, compound

Product 1

HCID 19888147HCID 19888147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.3 (25 mmol) of crude 3-amino-5-fluoro-2-hydroxybenzoic acid-(2,2,2,-trifluoro-ethyl)amide is dissolved in 30 ml of THF, 3.04 g (30 mmol) of triethylamine as well as 4.1 g (30 mmol) of acetoxyacetylchloride are added and stirred for 12 hours at room temperature. The reaction solution is then concentrated by evaporation in a vacuum and the residue is chromatographed on silica gel 60 with ethyl acetate/hexane. 5.52 g=62.7% of the theoretical yield is obtained as an amorphous solid.

Workup

  1. concentrationThe reaction solution is then concentrated by evaporation in a vacuum
  2. customthe residue is chromatographed on silica gel 60 with ethyl acetate/hexane
  3. custom5.52 g=62.7% of the theoretical yield
  4. customis obtained as an amorphous solid

Sources & evidence

ORD record
ord-3bfdc34d205c43dab7542e3f30791b57
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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