Water → HCID 178515622, compound

HRID 1276601Notes

Reaction equation

HRID 1276601 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-b352b3b8e9594aafb27517c881c04548
Source dataset
uspto-grants-2000_12
Patent number
US06166203

Reaction notes

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