N-bromobutanimide → HCID 53640973, compound

HRID 904835Notes

Reaction equation

HRID 904835 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[N:6]1[C:10]2[CH:11]=[C:12]([C:15](=[CH2:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH2:23].[Br:24]N1C(=O)CCC1=O>O1CCCC1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[N:6]1[C:10]2[CH:11]=[C:12]([C:15](=[CH:22][Br:24])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH2:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20477712HCID 20477712, compound

Product 1

HCID 53640973HCID 53640973, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.6 g. (5 mM) of 1-(thiazolin-2-yl)-2-amino-6-(α-methylenebenzyl)benzimidazole in 150 ml. of tetrahydrofuran were added in one portion 900 mg. (0.5 mM) of N-bromosuccinimide. The reaction mixture was stirred at room temperature for seventy-two hours, and then was concentrated to a volume of about 10 ml. by evaporation of the solvent under reduced pressure. The reaction mixture was diluted with 20 ml. of water, and the crystalline precipitate that formed was collected by filtration and identified as 600 mg. of 1-(thiazolin-2-yl)-2-amino-6-(α-bromomethylenebenzyl)benzimidazole. M.P. 197°-199° C. Yield 30%.

Workup

  1. concentrationwas concentrated to a volume of about 10 ml
  2. customby evaporation of the solvent under reduced pressure
  3. additionThe reaction mixture was diluted with 20 ml
  4. customof water, and the crystalline precipitate that formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-12c91b8260ff46f1b0dc9265a0044ddc
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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