Ethyl orthopropionate → HCID 136149349, compound

HRID 374088Notes

Reaction equation

HRID 374088 reaction equation
[NH2:1][C:2]1[N:3]([CH3:11])[C:4](=[S:10])[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:12](OCC)(OCC)(OCC)[CH2:13][CH3:14]>C(OC(=O)C)(=O)C>[CH2:13]([C:14]1[NH:9][C:7](=[O:8])[C:6]2[S:5][C:4](=[S:10])[N:3]([CH3:11])[C:2]=2[N:1]=1)[CH3:12]

Participants

4

Reactant 2

HCID 66995Ethyl orthopropionateHCID 1920193HCID 1920193, compound

Product 1

HCID 136149349HCID 136149349, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The general procedure of Gewald, J. Prakt. Chem., 32, 26-30 (1966) was used to prepare 4-amino-3-methylthiazoline-2-thione-5-carboxamide, of which 27.3 g (0.14 mole) was suspended in a mixture of approximately 144 ml of acetic anhydride and about 144 ml of triethyl orthopropionate. The resultant mixture was refluxed for approximately one half hour, then cooled in an ice bath. The solid which precipitated was separated by filtration, washed with diethyl ether and dried in a vacuum oven at approximately 100° C. to provide 21.4 g (65%) of 5-ethyl-3-methyl-6H-thiazolo[4,5-d]pyrimidin-7-one-2thione. Infrared spectral analysis confirmed the structural assignment.

Workup

  1. temperaturecooled in an ice bath
  2. customThe solid which precipitated
  3. customwas separated by filtration
  4. washwashed with diethyl ether
  5. customdried in a vacuum oven at approximately 100° C.

Sources & evidence

ORD record
ord-b0712d8ec19f4c8d85809d99c3d94324
Source dataset
uspto-grants-1992_11
Patent number
US05166343

Reaction notes

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