Hydrochloric Acid → HCID 14677771, compound

HRID 1165936Notes

Reaction equation

HRID 1165936 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[N:6]([CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)[CH:7]=[CH:8][N:9]=1.CO.[ClH:21].[CH:22](=O)[CH2:23][CH3:24].C([BH3-])#N.[Na+].Cl>CO>[ClH:21].[ClH:21].[CH2:22]([NH:1][CH2:2][CH2:3][S:4][C:5]1[N:6]([CH2:10][C:11]2[CH:12]=[C:13]([F:18])[CH:14]=[C:15]([F:17])[CH:16]=2)[CH:7]=[CH:8][N:9]=1)[CH2:23][CH3:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 14677768HCID 14677768, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 14677771HCID 14677771, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(2-aminoethylthio)-1-(3,5-diflorobenzyl)imidazole (2.69 g, 0.010 mole) in absolute methanol (25 ml) is added 5 N hydrochloric acid methanol (1 ml, 0.005 mole) followed by propionaldehyde (4.25 g, 0.10 mole) and sodium cyanoborohydride (0.38 g, 0.006 mole). The reaction mixture is stirred at 25° C. for 72 hours and then concentrated hydrochloric acid is added until the pH is at least 2. The volatiles are removed in vacuo and then the residue is partitioned between water and ether. The layers are shaken together and separated, the pH of the aqueous extract is adjusted to greater than 10 with solid potassium hydroxide and then the product is extracted into ether. The ether extract is dried with anhydrous magnesium sulfate and then hydrogen chloride in ether is added slowly until a slight excess is present. The precipitated solid is filtered and recrystallized from ethanol-ether to give 2-(2-propylaminoethylthio)-1-(3,5-difluorobenzyl)imidazole dihydrochloride.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is partitioned between water and ether
  3. stirringThe layers are shaken together
  4. customseparated
  5. extractionthe pH of the aqueous extract
  6. extractionthe product is extracted into ether
  7. extractionThe ether extract
  8. dry with materialis dried with anhydrous magnesium sulfate
  9. additionhydrogen chloride in ether is added slowly until a slight
  10. filtrationThe precipitated solid is filtered
  11. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-fefbfffebb6f45a682e28fdaefd3ea2e
Source dataset
uspto-grants-1990_03
Patent number
US04912226

Reaction notes

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