Diethyl acetylenedicarboxylate → HCID 12899659, compound

HRID 1278324Notes

Reaction equation

HRID 1278324 reaction equation
[NH2:1][C:2]1[S:3][C:4]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:5][N:6]=1.[C:12]([C:19](OCC)=[O:20])#[C:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[N:7]1([C:4]2[S:3][C:2]3=[N:1][C:19](=[O:20])[CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:6]3[N:5]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 15000145-pyrrolidin-1-yl-1,3,4-thiadiazol-2-amine

Product 1

HCID 12899659HCID 12899659, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.5 g of 2-amino-5-pyrrolidino-1,3,4-thiadiazole were added to 300 ml of ethanol and mixed with 8.5 g of diethyl acetylenedicarboxylate. On heating for 10 to 20 minutes to about 50° to 60° C. a clear solution was obtained which after standing overnight at room temperature was evaporated in vacuo to dryness. The residue was triturated with a small amount of cold ethyl acetate, filtered off, washed with ether and then dried. 8.4 g (57.1% of the theoretical yield) of ethyl 2-pyrrolidino-7H-1,3,4-thiadiazolo-[3,2-a]pyrimidin-7-one-5-carboxylate were thus obtained.

Workup

  1. temperatureOn heating for 10 to 20 minutes to about 50° to 60° C. a clear solution
  2. customwas obtained which
  3. customwas evaporated in vacuo to dryness
  4. customThe residue was triturated with a small amount of cold ethyl acetate
  5. filtrationfiltered off
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-6c8ec7becabb412b8d028d98d173437d
Source dataset
uspto-grants-1981_07
Patent number
US04281120

Reaction notes

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