Water → HCID 14013946, compound

HRID 1763164Notes

Reaction equation

HRID 1763164 reaction equation
[F:1][CH:2]([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([NH:15][CH3:16])=O)=[C:5]([NH:17][CH:18]([CH3:20])[CH3:19])[C:4]=1[C:21]([O:23][CH3:24])=[O:22].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1.O>C1(C)C=CC=CC=1>[F:1][CH:2]([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([NH:15][CH3:16])=[S:35])=[C:5]([NH:17][CH:18]([CH3:20])[CH3:19])[C:4]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 14013943HCID 14013943, compound

Product 1

HCID 14013946HCID 14013946, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3 g (0.009 mol) of product of Example 201 and 7.28 g (0.018 mol) of Lawesson's reagent in 100 ml of toluene was refluxed for 16 days. The reaction mixture was cooled to 25° C., poured into H2O, and extracted with ethyl acetate. The organic phase was dried (MgSO4), and concentrated in vacuo to 1.4 g of a brown oil. Chromatography using 10% ethyl acetate/cyclohexane as an eluting solvent afforded 0.35 g (11%) of product as a beige solid: mp 129°-131° C.

Workup

  1. temperaturewas refluxed for 16 days
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo to 1.4 g of a brown oil

Sources & evidence

ORD record
ord-e7281bcdeed64fd2b04a0e941e0a3b93
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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