Acetic Acid → HCID 56628153, compound

HRID 1388678Notes

Reaction equation

HRID 1388678 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:8]([OH:10])[CH3:9])[CH:5]=[N:4][C:3]=1[C:17]#[N:18].[OH-].[K+].[SH2:21].C(O)(=O)C>CO.O>[NH2:1][C:2]1[N:6]([CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:8]([OH:10])[CH3:9])[CH:5]=[N:4][C:3]=1[C:17](=[S:21])[NH2:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 402Hydrogen SulfideHCID 14797Potassium HydroxideHCID 14888759HCID 14888759, compound

Product 1

HCID 56628153HCID 56628153, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of erythro 5-amino-1-(2-hydroxynon-3-yl)-1H-imidazole-4-carbonitrile (1.02 g; 0.004 m) and potassium hydroxide (0.91 g; 0.163 m) in dry methanol (80 ml) was cooled to 0°, saturated with hydrogen sulphide, and heated to 100° for 5 hours. After cooling to 0°, nitrogen was passed through the solution to remove excess hydrogen sulphide and the residue was evaporated in vacuo to give a yellow solid. This solid was suspended in water and acetic acid added dropwise to pH5. The resulting precipitate was collected by filtration and washed with water. The residue was dissolved in dichloromethane/ethyl acetate, dried (Na2SO4) and evaporated in vacuo to give a white solid (1.22 g). Recrystallisation from ethyl acetate/charcoal gave a pale yellow solid, which was triturated in ether to give the product as white crystals (0.74 g) mp 170°-171°.

Workup

  1. temperatureheated to 100° for 5 hours
  2. temperatureAfter cooling to 0°
  3. customto remove excess hydrogen sulphide
  4. customthe residue was evaporated in vacuo
  5. customto give a yellow solid
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. dissolutionThe residue was dissolved in dichloromethane/ethyl acetate
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-2103b2e1b5b54ab8929397cc52f43c53
Source dataset
uspto-grants-1984_02
Patent number
US04432990

Reaction notes

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