Diethyl Ether → benzyl N-[(3R)-2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate

HRID 2068535Notes

Reaction equation

HRID 2068535 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.O=[C:24]1[C@H:30]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29][CH2:28][C:27]2[CH:42]=[CH:43][CH:44]=[CH:45][C:26]=2[NH:25]1.CCOCC>O1CCCC1>[S:10]=[C:24]1[C@H:30]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29][CH2:28][C:27]2[CH:42]=[CH:43][CH:44]=[CH:45][C:26]=2[NH:25]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 87949Lawesson's reagentHCID 58304068Benzyl N-[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate

Product 1

HCID 58304042benzyl N-[(3R)-2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add Lawesson's Reagent (12.25 g, 30.29 mmol) to a solution of benzyl N-[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate (9.4 g, 30.29 mmol) in tetrahydrofuran (470 mL) and stir the reaction under nitrogen for approximately 16 hours at ambient temperature. Remove the precipitate by filtration and discard it. Concentrate the filtrate under reduced pressure and dissolve the residue in ethyl acetate. Wash with water and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure to give a thick, yellow oil. Add ether to the thick oil and scratch it to form a solid. Collect the solid by filtration and wash it with ether. Triturate the solid with ether and collect it by filtration to give the title compound (7.28 g, 74%) as a white solid: MS (m/z): 349 (M+23).

Workup

  1. customthe reaction under nitrogen for approximately 16 hours at ambient temperature
  2. customRemove the precipitate
  3. filtrationby filtration
  4. concentrationConcentrate the filtrate under reduced pressure
  5. dissolutiondissolve the residue in ethyl acetate
  6. washWash with water and brine
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate the organic layer under reduced pressure
  9. customto give a thick, yellow oil
  10. customCollect the solid
  11. filtrationby filtration
  12. washwash it with ether
  13. customTriturate the solid with ether
  14. customcollect it
  15. filtrationby filtration

Sources & evidence

ORD record
ord-b4baf5bf2060485d99ca5d2d98a2e19e
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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