Diethyl acetylenedicarboxylate → HCID 53970052, compound

HRID 1732302Notes

Reaction equation

HRID 1732302 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1.[CH2:15]([O:17][C:18]([C:20]#[C:21][C:22](OCC)=[O:23])=[O:19])[CH3:16]>C(O)C>[CH2:15]([O:17][C:18]([C:20]1[N:6]2[N:5]=[C:4]([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:3][C:2]2=[N:1][C:22](=[O:23])[CH:21]=1)=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 6767605-(2-Phenylethyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 53970052HCID 53970052, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.1 g of 2-amino-5-(β-phenylethyl)-1,3,4-thiadiazole are heated with 6.8 g of acetylene dicarboxylic acid diethyl ester in 100 ml of ethanol until a clear solution has formed. After standing overnight, the solution is concentrated by evaporation to dryness. The residue crystallises on triturating with ether. 2-(β-Phenylethyl)-7H-1,3,4-thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester melting at 95° to 98° C. is thus obtained.

Workup

  1. customhas formed
  2. concentrationthe solution is concentrated by evaporation to dryness
  3. customThe residue crystallises
  4. customon triturating with ether

Sources & evidence

ORD record
ord-0aaaccafc4eb4cbe823a1228e62850a4
Source dataset
uspto-grants-1980_12
Patent number
US04237136

Reaction notes

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