Lawesson's reagent → HCID 136166791, compound

HRID 2072703Notes

Reaction equation

HRID 2072703 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[CH:5]=[CH:4][C:3]=1[C:22]1[C:23]2[CH:32]=[CH:31][S:30][C:24]=2[NH:25][C:26](=O)[CH2:27][N:28]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[CH:5]=[CH:4][C:3]=1[C:22]1[C:23]2[CH:32]=[CH:31][S:30][C:24]=2[NH:25][C:26](=[S:42])[CH2:27][N:28]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 136098683HCID 136098683, compound

Product 1

HCID 136166791HCID 136166791, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 0.25 g (0.53 mmol) of the compound prepared in (e) above in 5 ml of toluene was added 0.13 g (0.32 mmol) of Lawesson's Reagent, and the resultant mixture was heated to 90° C. and maintained at this temperature for 3 hours. After cooling the reaction mixture to 25° C., the solvent it was diluted with 50 ml methylene chloride, washed successively with 1 ml of water and 10 ml of brine, dried over magnesium sulfate and evaporated. The crude residue was pruified by column chromatography on silica gel employing a mixture of ethyl acetate and hexane in 2:1 ratio as the eluent to yield an orange foam.

Workup

  1. temperaturemaintained at this temperature for 3 hours
  2. washwashed successively with 1 ml of water and 10 ml of brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additiona mixture of ethyl acetate and hexane in 2:1 ratio as the eluent
  6. customto yield an orange foam

Sources & evidence

ORD record
ord-9a1c5ed001b945c8bb9342c68758e7f0
Source dataset
uspto-grants-1990_04
Patent number
US04914096

Reaction notes

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