HCID 18400133, compound → HCID 178432209, compound

HRID 1019089Notes

Reaction equation

HRID 1019089 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:18]C(NCCN)=S)=[C:16]([CH3:17])[C:11]=2[N:10]=[C:9]1[CH3:25])=O)(C)(C)C>CO>[CH3:25][C:9]1[NH:10][C:11]2[C:16]([CH3:17])=[C:15]([NH:18][N:10]3[CH2:11][CH2:12][N:8]=[CH:9]3)[CH:14]=[CH:13][C:12]=2[N:8]=1

Participants

3

Reactant 1

HCID 18400133HCID 18400133, compound

Product 1

HCID 178432209HCID 178432209, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(1-t-butoxycarbonyl-2,4-dimethyl-5-benzimidazolyl)-N′-2-aminoethylthiourea (1.33 g, 3.66 mmol) and mercuric acetate (1.45 g, 4.54 mmol) in methanol (150 mL) is stirred at room temperature for 1 hour. The resulting black mixture is filtered on Celite with a methanol wash of the solids. The filtrate is rotary evaporated and the residue is purified by flash chromatography on a short pad of silica gel, eluting with 10% methanol/chloroform containing 1% of ammonium hydroxide. The product-containing fractions are collected and rotary evaporated to afford 2,4-dimethyl-5-(2-imidazolinylamino)benzimidazole as a white solid.

Workup

  1. filtrationThe resulting black mixture is filtered on Celite with a methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue is purified by flash chromatography on a short pad of silica gel
  5. washeluting with 10% methanol/chloroform containing 1% of ammonium hydroxide
  6. customThe product-containing fractions are collected
  7. customrotary evaporated

Sources & evidence

ORD record
ord-adb2593a0a524d12a05feee60979b4e2
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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