Sulfuric Acid → HCID 21272626, compound

HRID 1193570Notes

Reaction equation

HRID 1193570 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[C:12]([C:14]1[N:15]([CH2:19][C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:17][N:18]=1)#[N:13].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1>CCOCC.C(O)C.O1CCCC1>[C:25]1([CH3:35])[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[NH2:13][CH2:12][C:14]1[N:15]([CH2:19][C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:17][N:18]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 14478517HCID 14478517, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21272626HCID 21272626, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.9 Grams of lithium aluminum hydride was added to about 50 ml of dry tetrahydrofuran. Then 1.3 ml of sulfuric acid was added by means of a syringe with cooling. The resulting slurry was stirred at room temperature for 1 hour and then a tetrahydrofuran solution of 3.0 g of 2-cyano-1-(2-thienylmethyl)-1H-imidazole was added and the mixture was stirred for 16 hours. The reaction mixture was quenched with 1.9 ml of water, 1.9 ml of 15% aqueous sodium hydroxide solution, and 5.7 ml of water. The mixture was then filtered and the solid was washed with ethyl acetate. The filtrate was then partitioned between water and ethyl acetate. The ethyl acetate layer was separated, dried over sodium sulfate and concentrated to give a yellow oil. A solution of 0.7 g of this oil in 300 ml of ether was prepared and a solution of 3.6 g of 4-toluenesulfonic acid in ethanol was added. The solid which formed was separated by filtration and dried to give 2-aminomethyl-1-(2-thienylmethyl)-1H-imidazole 4-toluenesulfonate melting at about 129°-131° C.

Workup

  1. temperaturewith cooling
  2. stirringthe mixture was stirred for 16 hours
  3. customThe reaction mixture was quenched with 1.9 ml of water, 1.9 ml of 15% aqueous sodium hydroxide solution, and 5.7 ml of water
  4. filtrationThe mixture was then filtered
  5. washthe solid was washed with ethyl acetate
  6. customThe filtrate was then partitioned between water and ethyl acetate
  7. customThe ethyl acetate layer was separated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto give a yellow oil
  11. customThe solid which formed
  12. customwas separated by filtration
  13. customdried

Sources & evidence

ORD record
ord-e581c52f8a33478aa34c6f39000abf75
Source dataset
uspto-grants-1989_03
Patent number
US04810800

Reaction notes

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