Lawesson's reagent → HCID 58687469, compound

HRID 2052769Notes

Reaction equation

HRID 2052769 reaction equation
[CH2:1]([O:5][C:6]1[C:15]([F:16])=[C:14]2[C:9]([C:10]3[CH:21]=[CH:20][C:19]([CH:22]4[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:24][CH2:23]4)=[C:18]([F:33])[C:11]=3[C:12](=O)[O:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1>ClC1C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:15]([F:16])=[C:14]2[C:9]([C:10]3[CH:21]=[CH:20][C:19]([CH:22]4[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:24][CH2:23]4)=[C:18]([F:33])[C:11]=3[C:12](=[S:43])[O:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58687472HCID 58687472, compound

Product 1

HCID 58687469HCID 58687469, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

11.7 g (25.6 mmol) of 3-butoxy-4,7-difluoro-8-(4-pentylcyclohexyl)-benzo[c]chromen-6-one and 11.4 g (28.2 mmol) of Lawesson's reagent were refluxed for 16 hours in 130 ml of chlorobenzene. The solution was subsequently filtered through silica gel and evaporated, and the crude product was purified by crystallisation from MTB ether, giving 7.9 g (65%) of 3-butoxy-4,7-difluoro-8-(4-pentylcyclohexyl)benzo[c]chromene-6-thione as yellow crystals.

Workup

  1. filtrationThe solution was subsequently filtered through silica gel
  2. customevaporated
  3. customthe crude product was purified by crystallisation from MTB ether

Sources & evidence

ORD record
ord-fb0d8d027bae4846bae619fed066a54b
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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