Sodium Chloride → HCID 22004124, compound

HRID 1603854Notes

Reaction equation

HRID 1603854 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[CH:24]=[CH:23][C:13]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=[N:16][C:12]=2[CH:11]=1.[Na+].[Cl-:26]>CN(C=O)C>[ClH:26].[Br:1][C:11]1[C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]=2[CH:23]=[CH:24][C:10]=1[OH:9]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 67184N-bromobutanimideHCID 6676621-Phenyl-1H-benzimidazol-5-ol

Product 1

HCID 22004124HCID 22004124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (0.72 g, 4.04 mmol) in DMF (5 mL) was added dropwise at room temperature to a solution of 5-hydroxy-1-phenylbenzimidazole (0.85 g, 4.04 mmol) in DMF (30 mL). After 1 hour the solution was diluted with aqueous NaCl and extracted into EtOAc, and the extract was worked up to give a solid which was chromatographed on silica gel. Elution with EtOAc/petroleum ether (1:1) gave foreruns, while EtOAc eluted Example 64 (0.88 g, 75%). HCl salt: mp (MeOH/Et2O) 244-246° C.

Workup

  1. extractionextracted into EtOAc
  2. customto give a solid which
  3. customwas chromatographed on silica gel
  4. washElution with EtOAc/petroleum ether (1:1)
  5. customgave foreruns
  6. washwhile EtOAc eluted Example 64 (0.88 g, 75%)
  7. custommp (MeOH/Et2O) 244-246° C.

Sources & evidence

ORD record
ord-f0da1aa412fc4b4689ddbcc04f25ce8e
Source dataset
uspto-grants-1999_11
Patent number
US05990146

Reaction notes

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