Acetic Acid → HCID 18671025, compound

HRID 1057251Notes

Reaction equation

HRID 1057251 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[CH2:9]([O:11][CH2:12][N:13]1[CH:20]=[CH:19][C:17](=O)[NH:16][C:14]1=[S:15])[CH3:10].C1([S:27]SC2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.O1C[CH2:42][CH2:41][CH2:40]1>C(OCC)(=O)C>[CH2:9]([O:11][CH2:12][N:13]1[C:20]([C:6]2[CH:5]=[CH:7][CH:42]=[CH:41][CH:40]=2)=[CH:19][C:17](=[S:27])[NH:16][C:14]1=[S:15])[CH3:10]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8028Tetrahydrofuran4×HCID 13436Diphenyl disulfideHCID 2724682Lithium diisopropylamideHCID 18671029HCID 18671029, compound

Product 1

HCID 18671025HCID 18671025, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

Then, 3.3 ml lithium diisopropylamide solution in tetrahydrofuran (2.1M) was added to 9 ml of tetrahydrofuran under a nitrogen atmosphere at −70° C., to which a solution of 0.56 g (3.0 mmol) of 1-ethoxymethyl-2-thiouracil in 3 ml of tetrahydrofuran was added dropwise over 15 minutes. After stirring for 1 hour at −70° C., the reaction mixture was added with a solution of 0.85 g (3.9 mmol) of diphenyl disulfide in 1 ml of tetrahydrofuran dropwise over 10 minutes and allowed to react for 20 minutes. The reaction mixture was added with 1 ml of acetic acid, brought to room temperature and then added with 30 ml of ethyl acetate. The mixture was washed with water (3 ml×5) and saturated aqueous solution of sodium hydrogencarbonate (twice), dried on magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17), crystallized from ethyl acetate to obtain 0.64 g of 1-ethoxymethyl-6-phenylthio-2-thiouracil (Yield: 73%).

Workup

  1. additionwas added dropwise over 15 minutes
  2. customto react for 20 minutes
  3. custombrought to room temperature
  4. washThe mixture was washed with water (3 ml×5) and saturated aqueous solution of sodium hydrogencarbonate (twice),
  5. customdried on magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17)
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-037a4671fd454eaea8e1b443c297112d
Source dataset
uspto-grants-2003_02
Patent number
USRE037979E1

Reaction notes

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