Ethyl orthopropionate → HCID 136149349, compound

HRID 1534351Notes

Reaction equation

HRID 1534351 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 144ml of acetic anhydride and about 144ml 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 21.4g (65%) of 5-ethyl-3-methyl-6H-thiazolo[4,5-d]pyrimidin-7-one-2-thione. 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-2d4009841cf94665ac1a451e3b626f30
Source dataset
uspto-grants-1992_02
Patent number
US05089493

Reaction notes

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