p-Chlorothiophenol → HCID 18374270, compound

HRID 2300035Notes

Reaction equation

HRID 2300035 reaction equation
Cl[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[C:3]=1[C:11]([C:13]1[C:14]([CH3:23])=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)=[O:12].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([SH:47])=[CH:43][CH:42]=1>C(Cl)Cl>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47][C:2]2[CH:8]3[CH2:9][CH:5]([CH2:6][CH2:7]3)[C:4](=[O:10])[C:3]=2[C:11]([C:13]2[C:14]([CH3:23])=[N:15][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:17][CH:18]=2)=[O:12])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 183742654-Chloro-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

Product 1

HCID 18374270HCID 18374270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (0.0058 mol) of 4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one, 0.07 g of dimethylaminopyridine (0.00058 mol) and 1.61 ml of triethylamine are dissolved in 15 ml of methylene chloride. At 25° C., 0.092 g (0.0064 mol) of 4-chlorothiophenol are added. After 2 hours at 22° C., the reaction mixture is evaporated and purified over silica gel (hexane/ethyl acetate 2:1). Recrystallization (hexane/acetic acid at −25° C.) gives pure 4-(4-chlorophenylsulfanyl)-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one: m.p. 130-131 ° C.

Workup

  1. customthe reaction mixture is evaporated
  2. custompurified over silica gel (hexane/ethyl acetate 2:1)
  3. customRecrystallization (hexane/acetic acid at −25° C.)

Sources & evidence

ORD record
ord-378d919d30954ac18cfc0349280c9811
Source dataset
uspto-grants-2002_12
Patent number
US06498125B2

Reaction notes

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