Lawesson's reagent → HCID 58192775, compound

HRID 2092644Notes

Reaction equation

HRID 2092644 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([C:14]3=O)[CH2:12]1)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([C:14]3=[S:32])[CH2:12]1)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58192798(4-Oxo-adamantan-1-yl)-carbamic acid benzyl ester

Product 1

HCID 58192775HCID 58192775, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ketone 10A (240 mg, 0.8 mmol) and Lawesson reagent (200 mg, 0.48 mmol) in anhydrous toluene was heated at 70° C. for overnight. The solvent was removed under vacuum and the residue was purified by silica gel chromatography [Hexane:EtOAc 4:1(v/v)] to give the title compounds 10B (130 mg, 54%). LC-MS (ESR): m/z=316 (M+H)+.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by silica gel chromatography [Hexane:EtOAc 4:1(v/v)]

Sources & evidence

ORD record
ord-5d6659d154ad43ba97be5949c6d51e76
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

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