1-(7-Carboxy-7-hydroxymethylheptyl)imidazole hydrochloride → HCID 12870472, compound

HRID 67657Notes

Reaction equation

HRID 67657 reaction equation
[ClH:1].[C:2]([CH:5]([CH2:17]O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)([OH:4])=[O:3]>P(=O)(O)(O)O>[ClH:1].[C:2]([C:5](=[CH2:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)([OH:4])=[O:3]

Participants

3

Reactant 1

HCID 128704331-(7-Carboxy-7-hydroxymethylheptyl)imidazole hydrochloride

Product 1

HCID 12870472HCID 12870472, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

To 180 mg of 1-(7-carboxy-7-hydroxymethylheptyl)imidazole hydrochloride (prepared in Example 6(b)) was added 2 or 3 drops of phosphoric acid, and the mixture was reacted under reduced pressure at 160° C. for 5 hours. The reaction mixture was purified by column chromatography on cellulose using a mixture of n-butanol, water and acetic acid (8:10:1), and the obtained fraction was adjusted to pH 8 with a 1 N solution of sodium hydride in order to remove the contaminated phosphoric acid, and the resulting crystals was removed off. The same purification by column chromatography on cellulose was repeated to give 78 mg of the title compound having the following physical characteristics:

Workup

  1. customthe mixture was reacted under reduced pressure at 160° C. for 5 hours
  2. customThe reaction mixture was purified by column chromatography on cellulose using
  3. additiona mixture of n-butanol, water and acetic acid (8:10:1)
  4. customto remove the contaminated phosphoric acid
  5. customthe resulting crystals was removed off
  6. customThe same purification by column chromatography on cellulose

Sources & evidence

ORD record
ord-f1ac66549426429b9429235be888d3cb
Source dataset
uspto-grants-1982_08
Patent number
US04346099

Reaction notes

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