N-bromobutanimide → HCID 20429452, compound

HRID 615168Notes

Reaction equation

HRID 615168 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]3[N:17]([CH:18]=2)[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[S:14]3)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]3[N:17]([C:18]=2[Br:23])[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[S:14]3)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12926148HCID 12926148, compound

Product 1

HCID 20429452HCID 20429452, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 30 ml of chloroform were added 1.35 g of 2-(m-acetoxyphenyl)imidazo[2,1-b]benzothiazole and 0.94 g of N-bromosuccinimide and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was washed with ether and dried to provide 2-(m-acetoxyphenyl)-3-bromoimidazo[2,1-b]benzothiazole. The product was suspended in 50 ml of methanol and after adding thereto 4 ml of 0.84 normal methanol solution of potassium hydroxide, the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added acetic acid to acidify the mixture and then 50 ml of water was added to the mixture to form crystals, which were recovered by filtration and recrystallized from a mixture of methylcellosolve and water to provide 1.2 g of 3-bromo-2-(m-hydroxyphenyl)imidazo[2,1-b]benzothiazole.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with ether
  3. customdried

Sources & evidence

ORD record
ord-47f7deebf86f456fb8f77374cdd230fc
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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