HCID 15718785, compound → HCID 178488097, compound

HRID 2166125Notes

Reaction equation

HRID 2166125 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)=S>[Hg]=O.O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:11]([NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[N:10][C:3]=2[CH:4]=1

Participants

4

Reactant 1

HCID 15718785HCID 15718785, compound

Product 1

HCID 178488097HCID 178488097, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 44 parts of N-(2-amino-5-methoxyphenyl)-N'-(1-methyl-4-piperidinyl)thiourea, 38.9 parts of mercury(II) oxide and 270 parts of tetrahydrofuran was stirred and refluxed for 2 hours at reflux temperature. The reaction mixture was filtered while hot over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel first using a mixture of trichloromethane and methanol (95:5 by volume) and then a mixture of trichloromethane and methanol, saturated with ammonia, (85:15 by volume) as eluents. The pure fractions were collected and the eluent was evaporated, yielding 50.5 parts (100%) of 5-methoxy-N-(1-methyl-4-piperidinyl)-1H-benzimidazol-2-amine as a residue (interm. 27).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureat reflux temperature
  3. filtrationThe reaction mixture was filtered while hot over diatomaceous earth
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography over silica gel
  6. additiona mixture of trichloromethane and methanol (95:5 by volume)
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-939f27ad240c45b5b49fdfa90f601f7b
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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