Lawesson's reagent → HCID 86641534, compound

HRID 1516183Notes

Reaction equation

HRID 1516183 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:12]=2[NH:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:30]2)=CC=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:12]=2[NH:11][C:10](=[S:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67377785tert-Butyl 7-chloro-2-oxo-1,2,3,5-tetrahydro-4H-1,4-benzodiazepine-4-carboxylate

Product 1

HCID 86641534HCID 86641534, compoundYield 157.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-chloro-2-oxo-1,2,3,5-tetrahydro-benzo[1,4]diazepine-4-carboxylic acid tert-butyl ester (41.1 g, 0.139 mol) and 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (31.5 g, 0.0763 mol) in tetrahydrofuran (1100 ml) was heated at reflux for 3 h. The solvent was evaporated and the residue was triturated in tert-butyl methyl ether. The precipitate was removed by filtration and the filtrate was concentrated to dryness. The residue was crystallized from hot ethanol to give the title compound (37.5 g, 86.4%) as light yellow solid:

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated
  4. customthe residue was triturated in tert-butyl methyl ether
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated to dryness
  7. customThe residue was crystallized from hot ethanol

Sources & evidence

ORD record
ord-14b2a44116fa4641bc178517ba9bd2f3
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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