Lawesson's reagent → HCID 14547398, compound

HRID 543128Notes

Reaction equation

HRID 543128 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH2:22][C:21](=O)[N:11]3[CH2:12][CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[CH:10]3[CH2:9]2)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1>CN(P(N(C)C)(N(C)C)=O)C>[S:45]=[C:21]1[N:11]2[CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH:10]2[CH2:9][NH:8][CH2:22]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14547397HCID 14547397, compound

Product 1

HCID 14547398HCID 14547398, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 2-(triphenylmethyl)-4-oxo-1,2,3,4,6,7,8,12b-octahydropyrazino[2,1-a][2]benzazepine (0.66 g) and Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide) (0.29 g) in HMPA (10 ml) was heated to 80° under a nitrogen atmosphere. The mixture was stirred at this temperature for 3 hr, cooled and partitioned between water and diethyl ether. The organic layer was washed with water and evaporated to a yellow foam. This residue was dissolved in acetone (20 ml), cooled to 0° and concentrated hydrochloric acid (0.5 ml) added. After stirring at room temperature for 30 min the mixture was evaporated and the residue partitioned between dilute hydrochloric acid and chloroform. The aqueous fraction was basified with sodium carbonate and extracted with chloroform. This chloroform fraction was washed with brine, dried (K2CO3) and evaporated to give the title compound as a white solid.

Workup

  1. temperaturewas heated to 80° under a nitrogen atmosphere
  2. temperaturecooled
  3. custompartitioned between water and diethyl ether
  4. washThe organic layer was washed with water
  5. customevaporated to a yellow foam
  6. dissolutionThis residue was dissolved in acetone (20 ml)
  7. temperaturecooled to 0°
  8. additionconcentrated hydrochloric acid (0.5 ml) added
  9. stirringAfter stirring at room temperature for 30 min the mixture
  10. customwas evaporated
  11. customthe residue partitioned between dilute hydrochloric acid and chloroform
  12. extractionextracted with chloroform
  13. washThis chloroform fraction was washed with brine
  14. dry with materialdried (K2CO3)
  15. customevaporated

Sources & evidence

ORD record
ord-beb561a1870c4e54ad071d1378310695
Source dataset
uspto-grants-1987_04
Patent number
US04661489

Reaction notes

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