Hydrochloric Acid → 2-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]amino-3-hydroxypyridine dihydrochloride

HRID 464382Notes

Reaction equation

HRID 464382 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([O:18]CC2C=CC=CC=2)=[CH:16][CH:15]=[CH:14][N:13]=1.[ClH:26].C(OCC)(=O)C>CO>[ClH:26].[ClH:26].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 155952532-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]amino-3-benzyloxypyridine

Product 1

HCID 202120212-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]amino-3-hydroxypyridine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]amino-3-benzyloxypyridine (1.3 g; 0.0036 moles) was treated with conc. hydrochloric acid (10 ml) and heated to 60° for 4 hours. The reaction mixture was stripped in vacuo to a green oil, dissolved in methanol, treated with ethyl acetate and left to stand for 2 days. The red crystals obtained were filtered off and recrystallised from methanol/ethyl acetate to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-3-hydroxypyridine dihydrochloride as dark red crystals (0.17 g, mp 210°-212°).

Workup

  1. temperatureheated to 60° for 4 hours
  2. waitleft
  3. customThe red crystals obtained
  4. filtrationwere filtered off
  5. customrecrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-5ca3ed3074b4496fa4505d307f640b50
Source dataset
uspto-grants-1985_10
Patent number
US04547512

Reaction notes

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