Lawesson's reagent → 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepine-5(4H)-thione monohydrochloride

HRID 364392Notes

Reaction equation

HRID 364392 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=O)[C:7]2[CH:13]=[N:14][CH:15]=[CH:16][C:6]=2[O:5]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:26])[C:7]2[CH:13]=[N:14][CH:15]=[CH:16][C:6]=2[O:5]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 137264002-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one

Product 1

HCID 137264022-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepine-5(4H)-thione monohydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one, 15 g (0.06 mole), was dissolved in 200 ml of dry toluene and 15 g (0.037 mole) of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide was added. The mixture was refluxed for 2.5 hr and the toluene solution decanted. The residue was partitioned between dilute sodium hydroxide and chloroform. The chloroform was dried and concentrated. The residue was chromatographed on a high pressure liquid chromatograph (Waters 500) using a silica column and eluting with ethyl acetate. The fraction containing material of molecular weight 257 was concentrated. The residue in isopropyl alcohol was treated with hydrogen chloride and the resulting crystals were collected. Yield of hydrochloride salt was 0.1 g (0.6%), m.p. 168°-171° C.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hr
  2. customthe toluene solution decanted
  3. customThe residue was partitioned between dilute sodium hydroxide and chloroform
  4. dry with materialThe chloroform was dried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a high pressure liquid chromatograph (Waters 500)
  7. washeluting with ethyl acetate
  8. additionThe fraction containing material of molecular weight 257
  9. concentrationwas concentrated
  10. additionThe residue in isopropyl alcohol was treated with hydrogen chloride
  11. customthe resulting crystals were collected

Sources & evidence

ORD record
ord-1cd6f505d3834783b655471117a688b9
Source dataset
uspto-grants-1986_08
Patent number
US04604388

Reaction notes

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