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

HRID 542865Notes

Reaction equation

HRID 542865 reaction equation
[CH2:1]([O:3][CH2:4]Cl)[CH3:2].[OH-].[Na+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([C:29]3[NH:30][CH:31]=[CH:32][CH:33]=3)[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:12][CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:17]=[C:18]([C:29]3[N:30]([CH2:4][O:3][CH2:1][CH3:2])[CH:31]=[CH:32][CH:33]=3)[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 18523Chloromethyl ethyl etherHCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-

Product 1

HCID 3063491Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(ethoxymethyl)-1H-pyrrol-2-yl)-Yield 48%

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), chloromethyl ethyl ether (0.57 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 20 minutes. 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) and is recrystallized from n-hexane to give 4,5-bis(4-methoxyphenyl)-2-(1-ethoxymethylpyrrol-2-yl)thiazole (1.01 g, yield: 48%).

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
  6. customis recrystallized from n-hexane

Sources & evidence

ORD record
ord-fabfb3feb47343308388872bfba61fc4
Source dataset
uspto-grants-1987_04
Patent number
US04659726

Reaction notes

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