Ethyl Acetate → 2-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamide

HRID 1180766Notes

Reaction equation

HRID 1180766 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15]#[N:16])[CH2:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([S:19]P([O-])(OCC)=S)C.C(OCC)(=O)C>O1CCCC1.O>[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15](=[S:19])[NH2:16])[CH2:11][CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11148614{1-[(Benzyloxy)methyl]cyclobutyl}acetonitrileHCID 53249491Diethyldithiophosphate

Product 1

HCID 112651762-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamideYield 71.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.7 g (45 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}acetonitrile in 100 mL of tetrahydrofuran and 10 mL of water was added 15.13 mL (90.2 mmol) of diethyldithiophosphate and the contents heated at reflux for 16 h. Ethyl acetate and water were added, and the layers separated. The organic phase was dried using magnesium sulfate and concentrated under vacuum to afford the crude product, which was purified by silica gel chromatography using ethyl acetate:hexane (2:8) as the eluent to afford 8.0 g (71%) of 2-{1-[(benzyloxy)methyl]cyclobutyl}ethanethioamide as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.00 (br s, 2H), 7.39-7.30 (m, 5H), 4.59 (s, 2H), 3.58 (s, 2H), 3.09 (s, 2H), 2.14-1.87 (m, 6H).

Workup

  1. temperaturethe contents heated
  2. temperatureat reflux for 16 h
  3. customthe layers separated
  4. customThe organic phase was dried
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-2e7c945452a44b5dbe56d6ed99610ada
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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