Diethyl acetylenedicarboxylate → HCID 53656289, compound

HRID 1732308Notes

Reaction equation

HRID 1732308 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.[CH2:8]([O:10][C:11]([C:13]#[C:14][C:15](OCC)=[O:16])=[O:12])[CH3:9]>C(O)C>[CH2:8]([O:10][C:11]([C:13]1[N:6]2[CH:5]=[C:4]([CH3:7])[S:3][C:2]2=[N:1][C:15](=[O:16])[CH:14]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 53656289HCID 53656289, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.4 g 2-amino-5-methylthiazole, 70 ml of ethanol and 5.1 g of acetylene dicarboxylic acid diethyl ester is left standing for 3 days. The solution is evaporated to dryness and the residue is triturated with ethyl acetate, crystallization occurring. The product is filtered off under suction, washed with ether and dried. The 2-methyl-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester thus obtained in a yield of 4.5 g (63% of the theoretical) melts at 119°-121° C.

Workup

  1. waitis left
  2. customThe solution is evaporated to dryness
  3. customthe residue is triturated with ethyl acetate, crystallization
  4. filtrationThe product is filtered off under suction
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-2f5d9297d72e4b3c89b0ded9a158f1d4
Source dataset
uspto-grants-1980_12
Patent number
US04237136

Reaction notes

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