Potassium Carbonate → 5,6-Bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

HRID 461836Notes

Reaction equation

HRID 461836 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[C:23]1(C)C=CC(S(OCCOS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=C[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]3[C:11]([S:22][CH2:23][CH2:24]3)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 228289Ethylene glycol ditosylateHCID 178489021HCID 178489021, compound

Product 1

HCID 128749955,6-Bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazoleYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 46.8 g (0.15 mole) of 4,5-bis(p-methoxyphenyl)-2-mercaptoimidazole, 55.5 g (0.15 mole) of ethylene glycol di-p-toluenesulfonate [Helv. Chim Acta 29 1675 (1946); Chem Abs. 41 1641 g] and 45.5 g (0.33 mole) potassium carbonate in 500 ml dimethylformamide was stirred at room temperature for 3 days. The mixture was poured into ice water and the precipitated product was collected and washed with water. Recrystallization from 1200 ml ethanol gave 31.3 g (61%) of product, m.p. 155°-8°.

Workup

  1. customthe precipitated product was collected
  2. washwashed with water
  3. customRecrystallization from 1200 ml ethanol

Sources & evidence

ORD record
ord-e09ad57bdfef492c87d73c085f8574c7
Source dataset
uspto-grants-1977_12
Patent number
US04064260

Reaction notes

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