Lawesson's reagent → HCID 86641534, compound

HRID 237335Notes

Reaction equation

HRID 237335 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 tort-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. MS m/e: 311 (M−H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated
  4. customthe residue was triturated in tort-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-ba2a3689e207451e884815fbebf5d9b0
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

Loading…