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

HRID 542868Notes

Reaction equation

HRID 542868 reaction equation
[CH2:1]([S:3][CH2:4][CH2:5]Br)[CH3:2].[OH-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([C:30]3[NH:31][CH:32]=[CH:33][CH:34]=3)[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:13][CH:12]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:18]=[C:19]([C:30]3[N:31]([CH2:2][CH2:1][S:3][CH2:4][CH3:5])[CH:32]=[CH:33][CH:34]=3)[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 2452961-Bromo-2-(ethylsulfanyl)ethaneHCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-

Product 1

HCID 3063495Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(2-(ethylthio)ethyl)-1H-pyrrol-2-yl)-Yield 89%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent2×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-bromoethyl ethyl sulfide (1.01 g, 6 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 4 hours. To the mixture are added water and benzene under ice-cooling, and the mixture is shaken. The benzene layer is taken, washed with water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue is subjected to silica gel column chromatography (solvent, ethyl acetate:cyclohexane=1:20) to give oily 4,5-bis(4-methoxyphenyl)-2-[1-(2-ethylthioethyl)pyrrol-2-yl]thiazole (2.01 g, yield: 89%).

Workup

  1. temperaturecooling
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-c9c31f7b31c5485e98a6dc11220711d9
Source dataset
uspto-grants-1987_04
Patent number
US04659726

Reaction notes

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