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Sodium Hydroxide → Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrol-2-yl)-

HRID 542864
Notes
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Reaction equation

HRID 542864 reaction equation
C1(C)C=CC(S(O[CH2:11][C:12]([F:15])([F:14])[F:13])(=O)=O)=CC=1.[OH-].[Na+].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[C:29]([C:40]3[NH:41][CH:42]=[CH:43][CH:44]=3)[S:30][C:31]=2[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:23][CH:22]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]=[C:29]([C:40]3[N:41]([CH2:11][C:12]([F:15])([F:14])[F:13])[CH:42]=[CH:43][CH:44]=3)[S:30][C:31]=2[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-

Product 1

HCID 3063472Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrol-2-yl)-Yield 36%

Reagents, catalysts & solvents 3

HCID 74236
Tetrabutylammonium Bromide
Catalyst
HCID 241BenzeneSolvent3×
HCID 962WaterSolvent

Procedure

4,5-Bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazole obtained in the same manner as described in Reference Example 6 (1.81 g, 5 mmole), 2,2,2-trifluoroethyl p-toluenesulfonate (1.27 g, 5 mmole), and tetra-n-butylammonium bromide (0.16 g, 0.5 mmole) are refluxed in two phases of benzene (20 ml) and 50% aqueous sodium hydroxide (20 ml) for 16 hours. To the mixture are added water and benzene under ice-cooling, and the mixture is shaken. The benzene layer is taken, and the aqueous layer is further extracted with benzene. The benzene layers are combined, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to give an oily residue. The oily residue is subjected to silica gel column chromatography (solvent: benzene) and then is recrystallized from n-hexane to give 4,5-bis(4-methoxyphenyl)-2-[1-(2,2,2-trifluoroethyl)pyrrol-2-yl]thiazole (0.80 g, yield: 36%).

Workup

  1. temperaturecooling
  2. extractionthe aqueous layer is further extracted with benzene
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto give an oily residue
  6. customis recrystallized from n-hexane

Sources & evidence

ORD record
ord-49bf1dff0b7540118d947cd6e67ad08e
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04659726

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes