1,2-Dibromoethane → HCID 13526427, compound

HRID 444294Notes

Reaction equation

HRID 444294 reaction equation
[CH3:1][S: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]([S:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[Br:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[BrH:23].[CH3:21][S:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]3[C:11]([S:22][CH2:24][CH2:25]3)=[N:10][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178503124HCID 178503124, compound

Product 1

HCID 13526427HCID 13526427, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 19.5 g. (0.06 mole) of 4,5-bis-(p-methylthiophenyl)-2-mercaptoimidazole, 10.7 g. (0.06 mole) of 1,2-dibromoethane and 7.9 g. (0.06 mole) of potassium carbonate in dimethylformamide (250 ml.) was refluxed for 3 hours. The mixture was then poured into 1 liter of ice-water and the yellow precipitate collected and washed with water. This material was then dissolved in chloroform, dried over magnesium sulfate, filtered and the solvent removed at reduced pressure. The residue was then treated with chloroform-ether and the white crystals of 5,6-bis(p-methylthiophenyl)-2,3-dihydroimidazo[2,1-b]thiazole collected. This was then dissolved in methanol and treated with aqueous hydrobromic acid. Filtering and recrystallizing from methanol gave 5,6-bis(p-methylthiophenyl)-2,3-dihydroimidazo[2,1-b]thiazole hydrobromide, m.p. 270° C.

Workup

  1. additionA mixture of 19.5 g
  2. customthe yellow precipitate collected
  3. washwashed with water
  4. dissolutionThis material was then dissolved in chloroform
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed at reduced pressure
  8. additionThe residue was then treated with chloroform-ether
  9. customthe white crystals of 5,6-bis(p-methylthiophenyl)-2,3-dihydroimidazo[2,1-b]thiazole collected
  10. dissolutionThis was then dissolved in methanol
  11. additiontreated with aqueous hydrobromic acid
  12. filtrationFiltering
  13. customrecrystallizing from methanol

Sources & evidence

ORD record
ord-1a11c80a071f450d8d20f9f7b9b00603
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Reaction notes

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