Hydrochloric Acid → HCID 178510004, compound

HRID 216599Notes

Reaction equation

HRID 216599 reaction equation
CO[CH:3](OC)[CH2:4][NH2:5].[N:8]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=1)=[C:9]=[S:10].Cl>O1CCOCC1>[SH:10][C:9]1[N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=2)[CH:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 183160684-Isothiocyanato-1-naphthonitrile

Product 1

HCID 178510004HCID 178510004, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

Aminoacetaldehyde dimethyl acetal (5.98 mL, 55.36 mmol) was added to a stirring slurry of 4-isothiocyanato-1-naphthonitrile (11.64 g, 55.36 mmol) in dioxane (55 mL), and stirring continued for 1 h (sizable exotherm observed). HCl was added (4.8 mL, 58.13 mmol) and the mixture heated to 105° C. for 18 h. The mixture was then concentrated, methanol added (100 mL), concentrated again, more methanol added (100 mL) and sonicated. Filtration provided 4-(2-mercapto-1H-imidazol-1-yl)-1-naphthonitrile as a tan solid (8.33 g, 60%).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionmethanol added (100 mL)
  3. concentrationconcentrated again
  4. additionmore methanol added (100 mL)
  5. customsonicated
  6. filtrationFiltration

Sources & evidence

ORD record
ord-c47fec08822b4d0780fd937e7a43b924
Source dataset
uspto-grants-2012_06
Patent number
US08193234B2

Reaction notes

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