6-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo(2,1-b)thiazole → SK&F 86096

HRID 46761Notes

Reaction equation

HRID 46761 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][S:11]3)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][S:11]3=[O:30])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 52286-(4-Fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)imidazo(2,1-b)thiazoleHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 469039SK&F 86096Yield 104.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.9 g of 6-(4-fluorophenyl)-5-(4-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole in 25 ml of methylene chloride cooled to ice-bath temperature was added 1.36 g of m-chloroperbenzoic acid. Stirring was continued for 1 hour then the solution was diluted with methylene chloride and washed with a 1:1 mixture of 5% sodium carbonate and brine. Treating with magnesium sulfate, filtering and stripping gave 2.1 g of the title product which was triturated with ether, filtered and dried to give 1.8 g, m.p.229°-231°.

Workup

  1. washwashed with a 1:1 mixture of 5% sodium carbonate and brine
  2. additionTreating with magnesium sulfate
  3. filtrationfiltering

Sources & evidence

ORD record
ord-82908142a84f455cbd81bd73fe0916ec
Source dataset
uspto-grants-1979_11
Patent number
US04175127

Reaction notes

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