Hydrochloric Acid → HCID 15124054, compound

HRID 1252495Notes

Reaction equation

HRID 1252495 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[F:11].CO[CH:14](OC)[CH2:15][NH2:16].Cl.[S-:20][C:21]#[N:22].[K+]>C(O)C.[Pd].CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:16]2[CH:15]=[CH:14][NH:22][C:21]2=[S:20])=[CH:5][C:4]=1[F:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 676963-Fluoro-p-anisaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516872Potassium thiocyanate

Product 1

HCID 15124054HCID 15124054, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-methoxy-3-fluorobenzaldehyde (15.4 g, 0.1 mol), aminoacetaldehyde dimethyl acetal (10.5 g, 0.1 mol), and methanol (1 ml) was heated at 95° C. for 10 minutes. The resulting mixture was dissolved in ethanol (150 ml) and hydrogenated over 10% Pd on carbon (1 g) until H2 uptake slowed (about 2 hours). The catalyst was filtered and the filtrate was treated with 1.5N hydrochloric acid (80 ml) and potassium thiocyanate (10.4 g, 0.11 mol). The resulting mixture was boiled until the volume was reduced to 100 ml, then it was heated at reflux an additional 1 hour and cooled to 5° C. The crystalline precipitate was filtered, washed with water, and dried. Recrystallization from ethanol gave 1-(4'-methoxy-3'-fluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione, 65% yield, m.p. 156°-157° C.

Workup

  1. custom(about 2 hours)
  2. filtrationThe catalyst was filtered
  3. temperatureit was heated
  4. temperatureat reflux an additional 1 hour
  5. temperaturecooled to 5° C
  6. filtrationThe crystalline precipitate was filtered
  7. washwashed with water
  8. customdried
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e1d4f203529a4a37922d3fb74857f023
Source dataset
uspto-grants-1988_05
Patent number
US04743613

Reaction notes

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