HCID 21472721, compound → HCID 69945089, compound

HRID 1736474Notes

Reaction equation

HRID 1736474 reaction equation
C(OC([N:8]1[C:12]2[C:13]([F:25])=[CH:14][C:15]([NH:18]C(NCCN)=S)=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C>CO>[F:25][C:13]1[C:12]2[N:8]=[CH:9][NH:10][C:11]=2[C:16]([CH3:17])=[C:15]([NH:18][N:10]2[CH2:11][CH2:12][N:8]=[CH:9]2)[CH:14]=1

Participants

3

Reactant 1

HCID 21472721HCID 21472721, compound

Product 1

HCID 69945089HCID 69945089, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(1-tert-butoxycarbonyl-7-fluoro-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthio-urea (0.5 g) and mercuric acetate (0.52 g) in methanol (150 mL) is stirred at room temperature for 1 hour. The resulting black mixture is filtered on Celite with methanol wash of the solids. The filtrate is rotary evaporated and the residue filtered through a short pad of silica gel, eluting 25% methanol in chloroform containing 1% of ammonium hydroxide. The product-containing fractions are rotary evaporated, the residue diluted with water (15 mL), filtered through a plug of glass wool and lyophilized to afford 7-fluoro-4-methyl-5-(2-imidazolinylamino)benzimidazole as a pale yellow solid.

Workup

  1. filtrationThe resulting black mixture is filtered on Celite with methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. filtrationthe residue filtered through a short pad of silica gel
  5. washeluting 25% methanol in chloroform containing 1% of ammonium hydroxide
  6. additionthe residue diluted with water (15 mL)
  7. filtrationfiltered through a plug of glass wool

Sources & evidence

ORD record
ord-a5a8efc387c140f2b2884fef9e5f5955
Source dataset
uspto-grants-1996_07
Patent number
US05541210

Reaction notes

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