Triethylamine → HCID 67200450, compound

HRID 550712Notes

Reaction equation

HRID 550712 reaction equation
C(O[C:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[NH2:11])=[O:5])C.C1N=CN([C:17]([N:19]2C=NC=C2)=[O:18])C=1.Cl.[CH2:25]([O:28]N)[CH:26]=[CH2:27].CCN(CC)CC>C1(C)C=CC=CC=1>[CH2:25]([O:28][N:19]1[C:4](=[O:5])[C:6]2[S:7][CH:8]=[CH:9][C:10]=2[NH:11][C:17]1=[O:18])[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 10261542Ethyl 3-aminothiophene-2-carboxylate

Product 1

HCID 67200450HCID 67200450, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Amino-thiophene-2-carboxylic acid ethyl ester (2 grams, 12.7 mmol) and CDI (2.3 g, 14 mmol) were refluxed 20 mL in toluene overnight. O-Allyl hydroxylamine hydrochloride (1.7 g, 15.5 mmol) and Et3N (2.2 mL, 15.5 mmol) were added and solution was again brought to reflux for 3 hours. The solution was cooled, concentrated, and redissolved in 25 mL hot ethanol. NaOH was added (16 mL of a 2 M aq. solution) and the mixture was heated to reflux for 1 hour. The reaction mixture was acidified with 1 mL of glacial acetic acid and cooled. The resultant precipitate was filtered and discarded. The filtrate was concentrated, treated with 20 mL of ethanol, sonicated briefly, and then filtered to give 1.3 grams of 3-allyloxy-1H-thieno[3,2-d]pyrimidine-2,4-dione.

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureThe solution was cooled
  3. concentrationconcentrated
  4. dissolutionredissolved in 25 mL hot ethanol
  5. additionNaOH was added (16 mL of a 2 M aq. solution) and the mixture
  6. temperaturewas heated
  7. temperatureto reflux for 1 hour
  8. temperaturecooled
  9. filtrationThe resultant precipitate was filtered
  10. concentrationThe filtrate was concentrated
  11. additiontreated with 20 mL of ethanol
  12. customsonicated briefly
  13. filtrationfiltered

Sources & evidence

ORD record
ord-3afdb9b976fa4a939937877e5b20d91d
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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