Chloroform → 1-Tert-butoxycarbonyl-4-methyl-5-(2-imidazolinylamino)benzimidazole

HRID 2260726Notes

Reaction equation

HRID 2260726 reaction equation
[C:1]([O:5][C:6]([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]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl>CO>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:18][N:10]3[CH2:11][CH2:12][N:8]=[CH:9]3)=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 21472715N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea

Product 1

HCID 677273531-Tert-butoxycarbonyl-4-methyl-5-(2-imidazolinylamino)benzimidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea (2.89 g) and mercuric acetate (3.32 g) in methanol (200 mL)/chloroform (100 mL) is stirred at room temperature for 2 hours. The resulting black mixture is filtered on Celite and the filtrate rotary evaporated. The residue is purified by flash chromatography on a short pad of silica gel, eluting with 10% methanol/chloroform containing 1% ammonium hydroxide. The product-containing fractions are collected and rotary evaporated to afford 1-tert-butoxycarbonyl-4-methyl-5-(2-imidazolinylamino)benzimidazole as a white solid.

Workup

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

Sources & evidence

ORD record
ord-74f15715e4214ca4bcc980faef51f541
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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