Lawesson's reagent → HCID 13726456, compound

HRID 247296Notes

Reaction equation

HRID 247296 reaction equation
O.[Cl:2][CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=O)[C:8]2[CH:14]=[CH:15][C:16]([CH3:18])=[N:17][C:7]=2[O:6]1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:28]2)=CC=1>C1(C)C=CC=CC=1>[OH2:6].[Cl:2][CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[S:28])[C:8]2[CH:14]=[CH:15][C:16]([CH3:18])=[N:17][C:7]=2[O:6]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 13726454HCID 13726454, compound

Product 1

HCID 13726456HCID 13726456, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 17.4 g (0.043 mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diposphetane-2,4-disulfide in ~300 ml of toluene was added 20 g (0.078 mole) of 2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one hydrate [1:1]. The mixture was heated to reflux for 3 hr and 4.0 g (0.01 mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide was added and heating was continued for 1 hr. After cooling, toluene was decanted off and washed with 3×100 ml 1N sodium hydroxide and 100 ml water. The organic layer was then extracted with 2×100 ml of 2N hydrochloric acid. The aqueous layer was made just basic to litmus with conc. sodium hydroxide causing the product to precipitate out. Of the 25 g of crude collected, 2 g were recrystallized from diisopropyl ether to give pale yellow crystals, m.p. 80°-86° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hr
  3. temperatureheating
  4. temperatureAfter cooling
  5. customtoluene was decanted off
  6. washwashed with 3×100 ml 1N sodium hydroxide and 100 ml water
  7. extractionThe organic layer was then extracted with 2×100 ml of 2N hydrochloric acid
  8. customto precipitate out
  9. customOf the 25 g of crude collected
  10. custom2 g were recrystallized from diisopropyl ether
  11. customto give pale yellow crystals, m.p. 80°-86° C.

Sources & evidence

ORD record
ord-ae1c250c2f4d442198cd56c153e67908
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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