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

HRID 1906470Notes

Reaction equation

HRID 1906470 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10]C1C(OCC2C=CC=CC=2)=C(N)C=CN=1.[ClH:26].C(O[CH2:31][CH3:32])(=O)C.[CH3:33][OH:34]>>[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:6][C:5]1[C:33]([OH:34])=[CH:32][CH:31]=[CH:3][N:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 704313152-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]-amino3-benzyloxypyridine

Product 1

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

Procedure

2-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]-amino3-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-9a945ce469f84efe96a4a0300b445ea3
Source dataset
uspto-grants-1987_03
Patent number
US04652572

Reaction notes

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