Lawesson's reagent → HCID 86667991, compound

HRID 593347Notes

Reaction equation

HRID 593347 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13]1[CH:14]=[C:15]([C:19]2([CH3:26])[NH:24][C:23](=O)[CH2:22][O:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13]1[CH:14]=[C:15]([C:19]2([CH3:26])[NH:24][C:23](=[S:36])[CH2:22][O:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68107950HCID 68107950, compound

Product 1

HCID 86667991HCID 86667991, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (RS)-5-[3-(3-chloro-quinolin-8-ylamino)-phenyl]-5-methyl-morpholin-3-one (368 mg, 1.1 mmol) in tetrahydrofuran was treated with Lawesson's reagent (500 mg, 1.2 mmol) at room temperature during 3 hours. The progress of the reaction was checked by LC-MS. For the workup, the reaction mixture was evaporated at reduced pressure. The residue was partitioned between water (5 ml) and ethyl acetate (5 ml), then the organic layer separated, dried over sodium sulphate and evaporated. The crude product was purified by flash chromatography on silica gel using a gradient of cyclohexane/ethyl acetate as the eluent yielding 300 mg (71%) of (RS)-5-[3-(3-chloro-quinolin-8-ylamino)-phenyl]-5-methyl-morpholine-3-thione; (calculated) C20H18ClN3OS [383.90]; (found) [M+H]+=384.

Workup

  1. customFor the workup, the reaction mixture was evaporated at reduced pressure
  2. customThe residue was partitioned between water (5 ml) and ethyl acetate (5 ml)
  3. customthe organic layer separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel using a gradient of cyclohexane/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-074d2ecfec4445b4aa799d53a96f8141
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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