Acetic Acid → HCID 86749177, compound

HRID 2295052Notes

Reaction equation

HRID 2295052 reaction equation
[CH3:1]C(O)=O.[CH3:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([N:16]=C=S)=[C:14]([CH3:15])[C:9]=2[N:8]=[CH:7]1.[CH2:19]([NH2:22])[CH2:20][NH2:21]>C(Cl)Cl.CO>[CH3:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([NH:16][N:21]3[CH2:20][CH2:19][N:22]=[CH:1]3)=[C:14]([CH3:15])[C:9]=2[N:8]=[CH:7]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 153408751,4-Dimethyl-5-benzimidazolylisothiocyanate

Product 1

HCID 86749177HCID 86749177, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

HOAc. A solution of 1,4-dimethyl-5-benzimidazolylisothiocyanate (210 mg) in methylene chloride (40 mL) is added dropwise over 20 minutes to ethylenediamine (0.35 mL) in solution in methylene chloride (100 mL). The mixture is stirred for 1 hour at room temperature, then rotary evaporated. The residue is dissolved in methanol (70 mL), mercuric acetate (395 mg) is added, and the mixture is stirred at room temperature for 2 hours. The resulting black suspension is filtered on Celite with methanol wash of the solids. The filtrate is rotary evaporated, and the residue is purified by flash chromatography on silica gel, eluting with 10% methanol/chloroform containing 0.1% of ammonium hydroxide. The product-containing fractions are combined and rotary evaporated to yield 1,4-dimethyl-5-(2-imidazolinylamino)benzimidazole.HOAc.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. filtrationThe resulting black suspension is filtered on Celite with methanol
  3. washwash of the solids
  4. customthe residue is purified by flash chromatography on silica gel
  5. washeluting with 10% methanol/chloroform containing 0.1% of ammonium hydroxide
  6. customrotary evaporated

Sources & evidence

ORD record
ord-dfe4b6f1a8c84598a1c9db6b102fcb20
Source dataset
uspto-grants-1997_11
Patent number
US05691370

Reaction notes

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