Water → HCID 178515622, compound

HRID 2230079Notes

Reaction equation

HRID 2230079 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.[F:10][C:11]1[CH:24]=[CH:23][C:14]([C:15]([CH2:17]C(OCC)=O)=O)=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:10][C:11]1[CH:24]=[CH:23][C:14]([C:15]2[N:1]=[C:2]3[CH:6]=[CH:5][S:4][C:3]3=[C:7]([OH:9])[CH:17]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 15124973-Amino-2-thiophenecarboxylic acidHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Product 1

HCID 178515622HCID 178515622, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-amino-2-thiophenecarboxylic acid (8 g, 49 mmol), ethyl 4-fluorobenzoylacetate (9.6 g, 49 mmol), and p-toluenesulfonic acid monohydrate (0.2 g, 1 mmol) in toluene (100 mL) is refluxed for 20 hours with a Dean-Stark water trap to remove produced water. The mixture is cooled to room temperature. The resulting precipitate is filtered and washed with diethyl ether. The solid is dissolved in diphenyl ether (80 mL) and heated at 220° C. for 2 hours. The reaction solution is then cooled to room temperature and diluted with diethyl ether; the precipitate is filtered and washed with diethyl ether to give 5-(4-fluorophenyl)-thieno[3,2-b]pyridin-7-ol (2 g, 17% yield) as brown crystalline needles, m.p. 316-318° C.

Workup

  1. customto remove
  2. customproduced water
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with diethyl ether
  5. dissolutionThe solid is dissolved in diphenyl ether (80 mL)
  6. temperatureheated at 220° C. for 2 hours
  7. temperatureThe reaction solution is then cooled to room temperature
  8. additiondiluted with diethyl ether
  9. filtrationthe precipitate is filtered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-020d0c20e9434b4fa04c6ed49427ee30
Source dataset
uspto-grants-2002_07
Patent number
US06423711B1

Reaction notes

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