Bromine → HCID 21516656, compound

HRID 268025Notes

Reaction equation

HRID 268025 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[NH:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[S:7])=[CH:2]1.BrBr>C(Cl)(Cl)Cl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][N:10]3[C:9](=[N:13][C:12]4[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=43)[N:8]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 24408BromineHCID 53664329HCID 53664329, compound

Product 1

HCID 21516656HCID 21516656, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 4.8 g. of 2-(3-furylthiocarbonylamino)-benzimidazole [(IV), R = 3-furyl] in 200 ml. of chloroform at 20°-30°C. (room temperature) is added 1.1 ml. of bromine. After 1 hour, the reaction mixture is filtered and the residue (the hydrobromide salt) is treated with 500 ml. of chloroform and 50 ml. of aqueous ammonia. The chloroform layer is separated, dried over magnesium sulfate, and concentrated. The product is recrystallized from methanol-chloroform to yield 2-(3-furyl)-1,2,4-thiadiazolo-[2,3-a]-benzimidazole [(I), R = 3-furyl].

Workup

  1. filtrationthe reaction mixture is filtered
  2. additionthe residue (the hydrobromide salt) is treated with 500 ml
  3. customThe chloroform layer is separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product is recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-953d77f109c748e4a819c8c23bf0fed9
Source dataset
uspto-grants-1976_03
Patent number
US03946031

Reaction notes

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