Acetamidine monohydrochloride → STK682706

HRID 703073Notes

Reaction equation

HRID 703073 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 135403592STK682706

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Ethyl 4-amino-3-methylthiazoline-2-thione-5-carboxylate (1.4g, 6.4 mmoles), prepared according to the procedure of Gewald, J. Prakt. Chem., 32, 26-30 (1966), was suspended in approximately 40ml of ethanol. Acetamidine hydrochloride (0.6g, 6.4 mmole) and 2.77g (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 1g 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-5536b2a3e43d414f9640a80fc7ec128f
Source dataset
uspto-grants-1991_01
Patent number
US04981850

Reaction notes

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