Diethyl acetylenedicarboxylate → HCID 54442780, compound

HRID 1732299Notes

Reaction equation

HRID 1732299 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=2)[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[C:5]([C:7]3[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=3)=[CH:4][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 7339084-(4-ethylphenyl)-1,3-thiazol-2-amine

Product 1

HCID 54442780HCID 54442780, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of 2-amino-4-(4'-ethylphenyl)-thiazole are dissolved in 50 ml of ethanol and 8.4 g of acetylene dicarboxylic acid diethyl ester are added to the resulting solution. After standing overnight, the mixture is concentrated by evaporation in vacuo to dryness at a bath temperature of 40° to 50° C. 50 ml of chlorobenzene are added to the residue, followed by heating unter reflux for 1 hour. After concentration by evaporation in vacuo, the residue is dissolved in ether, treated with carbon, filtered and petroleum ether subsequently added. The product precipitating is washed with a little ether and dried. 3-(4'-ethylphenyl)-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester melting at 142°-144° C. is thus obtained.

Workup

  1. concentrationthe mixture is concentrated by evaporation in vacuo to dryness at a bath temperature of 40° to 50° C
  2. addition50 ml of chlorobenzene are added to the residue
  3. temperatureby heating unter
  4. temperaturereflux for 1 hour
  5. concentrationAfter concentration
  6. customby evaporation in vacuo
  7. dissolutionthe residue is dissolved in ether
  8. additiontreated with carbon
  9. filtrationfiltered
  10. additionpetroleum ether subsequently added
  11. customThe product precipitating
  12. washis washed with a little ether
  13. customdried

Sources & evidence

ORD record
ord-f93ca90775914f9b960339052919eeb5
Source dataset
uspto-grants-1980_12
Patent number
US04237136

Reaction notes

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