1-Butanol → 5-Hydroxymethyl-2-mercapto-1-benzylimidazole

HRID 1380989Notes

Reaction equation

HRID 1380989 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3]C.C1OC(O)(CO)COC1(O)CO.[S-:18][C:19]#[N:20].[K+].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(=O)C>[CH2:22]([N:29]1[C:2]([CH2:1][OH:5])=[CH:3][N:20]=[C:19]1[SH:18])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 7504BenzylamineHCID 516872Potassium thiocyanateHCID 4180364Dihydroxyacetone dimer

Product 1

HCID 1785198455-Hydroxymethyl-2-mercapto-1-benzylimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

n-Butanol (50 ml), glacial acetic acid (25 g), dihydroxyacetone dimer (21.0 g), potassium thiocyanate (34.1 g) and benzylamine (28.0 g) are combined at room temperature. The mixture is stirred at room temperature for 50 hours and the product is filtered. A light brown product is obtained, 35.0 g (68.2%), m.p. 229°-231° C. The NMR spectrum shows:

Workup

  1. customare combined at room temperature
  2. filtrationthe product is filtered
  3. customA light brown product is obtained

Sources & evidence

ORD record
ord-b47689e520434a2d94579990bd6f6664
Source dataset
uspto-grants-1986_04
Patent number
US04584383

Reaction notes

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