Acetic Acid → HCID 675153, compound

HRID 1771930Notes

Reaction equation

HRID 1771930 reaction equation
C(O[C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:17])=[O:5])C.[O-:18][C:19]#[N:20].[K+].C(O)(=O)C>O>[C:11]1([C:10]2[C:6]3[C:4](=[O:5])[NH:20][C:19](=[O:18])[NH:17][C:7]=3[S:8][CH:9]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 11378442Potassium cyanate

Product 1

HCID 675153HCID 675153, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester (2.0 g, 8.1 mmol), and Potassium Cyanate (Aldrich, 2.0 g, 24.3 mmol) were added to glacial acetic acid (VWR, 20 ml) and stirred at ambient temperature for 18 h. The reaction was diluted with water (50 ml) and the resultant precipitate filtered, washed with water and dried to a damp cake. The solid was suspended in water (100 ml) and made alkaline to pH 12-14 by the addition of concentrated sodium hydroxide. The resultant suspension was heated at 100° C. for 2 h with stirring, then cooled to ambient temperature and acidified by the addition of glacial acetic acid. The resulting solid was collected by filtration, washed with water and dried in vacuo at 40° C. to give 5-Phenyl-1H-thieno[2,3-d]pyrimidine-2,4-dione as a white solid. Yield=(1.1 g, 56%).

Workup

  1. filtrationthe resultant precipitate filtered
  2. washwashed with water
  3. customdried to a damp cake
  4. additionby the addition of concentrated sodium hydroxide
  5. temperatureThe resultant suspension was heated at 100° C. for 2 h
  6. stirringwith stirring
  7. temperaturecooled to ambient temperature
  8. additionacidified by the addition of glacial acetic acid
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with water
  11. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-53277105ed4d417f80be9d84f7f8269f
Source dataset
uspto-grants-2016_02
Patent number
US09249155B2

Reaction notes

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