Lawesson's reagent → Benzyl N-(2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl)carbamate

HRID 2068539Notes

Reaction equation

HRID 2068539 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>C1(C)C=CC=CC=1>[S:10]=[C:24]1[CH: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

4

Reactant 2

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

Product 1

HCID 58304049Benzyl N-(2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl)carbamateYield 104.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add Lawesson's Reagent (6.52 g, 16.11 mmol) to a solution of benzyl N-[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate (10.0 g, 32.22 mmol) in toluene (120 mL) and heat the reaction under nitrogen at 100° C. for 2.5 hours. Allow the reaction to cool and collect the precipitate by filtration. Wash (ether) the cake and dry it in a vacuum oven to give the title compound (5.5 g, 16.8 mmol). Concentrate the filtrate under reduced pressure and purify it by flash chromatography (30% hexane/CH2Cl2 to 100% CH2Cl2) to give the title compound (3.48 g, 10.7 mmol). The compound is partially racemized. The total yield of the title compound is 85%: MS (m/z): 327 (M+1).

Workup

  1. temperatureheat
  2. customthe reaction under nitrogen at 100° C. for 2.5 hours
  3. customAllow the reaction
  4. temperatureto cool
  5. customcollect the precipitate
  6. filtrationby filtration
  7. washWash (ether) the cake
  8. customdry it in a vacuum oven

Sources & evidence

ORD record
ord-b9302d0afcde4c6cb1f7a44d1e7dec06
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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