Acetamidine monohydrochloride → STK682706

HRID 374089Notes

Reaction equation

HRID 374089 reaction equation
[NH2:1][C:2]1[N:3]([CH3:13])[C:4](=[S:12])[S:5][C:6]=1[C:7]([O:9]CC)=O.Cl.[C:15](N)(=[NH:17])[CH3:16].C[O-].[Na+]>C(O)C.CO>[CH3:13][N:3]1[C:2]2[N:1]=[C:15]([CH3:16])[NH:17][C:7](=[O:9])[C:6]=2[S:5][C:4]1=[S:12]

Participants

6

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 3241046HCID 3241046, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 135403592STK682706Yield 73.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Ethyl 4-amino-3-methylthiazoline-2-thione-5-carboxylate (1.4 g, 6.4 mmoles), prepared according to the procedure of Gewald, J. Prakt. Chem., 32, 26-30 (1966), was suspended in approximately 40 ml of ethanol. Acetamidine hydrochloride (0.6 g, 6.4 mmole) and 2.77 g (12.8 mmole) of a 25% solution of sodium methoxide in methanol were added to the suspension and the resultant mixture refluxed for approximately 20 hours. The ethanol was removed in vacuo and the residue was suspended in water and neutralized with concentrated hydrochloric acid. The resultant precipitate was filtered and dried to provide 1 g of 3,5-dimethyl-6H-thiazolo[4,5-d]pyrimidin-7-one-2-thione. The structural assignment was confirmed by nuclear magnetic resonance spectral analysis.

Workup

  1. customThe ethanol was removed in vacuo
  2. filtrationThe resultant precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-7a1c9fc95e984741b7fd2d6e765ac988
Source dataset
uspto-grants-1992_11
Patent number
US05166343

Reaction notes

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