m-Chloroperbenzoic acid → 6-(4-Methoxyphenyl)-5-(4-Pyridyl)-2,3-dihydroimidazo[2,1-b]Thiazole-1-Oxide

HRID 46760Notes

Reaction equation

HRID 46760 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:14][CH2:13][S:12]3)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:14][CH2:13][S:12]3=[O:31])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 151555166-(4-Methoxyphenyl)-5-(pyridin-4-yl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

Product 1

HCID 203855276-(4-Methoxyphenyl)-5-(4-Pyridyl)-2,3-dihydroimidazo[2,1-b]Thiazole-1-OxideYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 2.4 g of 6-(4-methoxyphenyl)-5-(4-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole in 200 ml methylene chloride was added 1.34 g of m-chloroperbenzoic acid in 150 ml of methylene chloride at ice-bath temperature. After 10 minutes the reaction mixture was diluted with methylene chloride and washed twice with 100 ml of 5 N sodium carbonate. Evaporation of the dried extracts left a solid which when recrystallized from chloroform-ether gave 1.6 g of the title product, m.p. 165°-170°.

Workup

  1. washwashed twice with 100 ml of 5 N sodium carbonate
  2. customEvaporation of the dried extracts
  3. waitleft a solid which when
  4. customrecrystallized from chloroform-ether

Sources & evidence

ORD record
ord-f7763a23836940bfbd0632da552168e5
Source dataset
uspto-grants-1979_11
Patent number
US04175127

Reaction notes

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