Lawesson's reagent → 7-Chloro-3,5-dihydrobenzo[e][1,4]oxazepine-2(1H)-thione

HRID 72175Notes

Reaction equation

HRID 72175 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=O)[CH2:8][O:9][CH2:10][C:4]=2[CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:23]2)=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[S:23])[CH2:8][O:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 840481997-Chloro-3,5-dihydrobenzo[e][1,4]oxazepin-2(1H)-one

Product 1

HCID 866797107-Chloro-3,5-dihydrobenzo[e][1,4]oxazepine-2(1H)-thioneYield 107.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-chloro-3,5-dihydrobenzo[e][1,4]oxazepin-2(1H)-one (3.01 g, 15.2 mmol) in tetrahydrofurane (102 ml) was added 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (3.45 g, 8.53 mmol) at room temperature. The reaction mixture was heated at reflux for 4 h. After cooling to room temperature the solvent was evaporated and the residue was crystallized from hot ethanol to give the title compound (1.96 g, 60%) as light yellow solid. MS m/e: 211.6 ([M−H]−).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. customwas evaporated
  4. customthe residue was crystallized from hot ethanol

Sources & evidence

ORD record
ord-2f39995c16374d908b14b95082549e1d
Source dataset
uspto-grants-2014_09
Patent number
US08828989B2

Reaction notes

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