Dimethyl acetylenedicarboxylate → HCID 54181417, compound

HRID 1732300Notes

Reaction equation

HRID 1732300 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[CH3:7][O:8][C:9]([C:11]#[C:12][C:13](OC)=[O:14])=[O:10]>O1CCCC1>[CH3:7][O:8][C:9]([C:11]1[N:6]2[N:5]=[CH:4][S:3][C:2]2=[N:1][C:13](=[O:14])[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 199091,3,4-Thiadiazol-2-amine

Product 1

HCID 54181417HCID 54181417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 ml of tetrahydrofuran are added to 10.1 g of 2-amino-1,3,4-thiadiazole, followed by the gradual introduction of 14.2 g of acetylene dicarboxylic acid dimethyl ester. The reaction mixture is left standing for 3 days, resulting in the formation of a clear, yellow colored solution. The solution thus formed is concentrated by evaporation in vacuo to dryness. Recrystallization of the residue from ethyl acetate gives 7H-1,3,4-thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid methyl ester melting at 134° C. with decomposition.

Workup

  1. waitThe reaction mixture is left
  2. customresulting in the formation of a clear, yellow colored solution
  3. customThe solution thus formed
  4. concentrationis concentrated by evaporation in vacuo to dryness
  5. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-62aa5a530022425b9b6c0b1c9955647d
Source dataset
uspto-grants-1980_12
Patent number
US04237136

Reaction notes

Loading…