2-Amino-4-phenylthiazole → HCID 13466428, compound

HRID 1732297Notes

Reaction equation

HRID 1732297 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH2:13]([O:15][C:16]([C:18]#[C:19][C:20](OCC)=[O:21])=[O:17])[CH3:14]>O1CCCC1>[CH2:13]([O:15][C:16]([C:18]1[N:6]2[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:4][S:3][C:2]2=[N:1][C:20](=[O:21])[CH:19]=1)=[O:17])[CH3:14]

Participants

4

Reactant 2

HCID 403022-Amino-4-phenylthiazoleHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 13466428HCID 13466428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

17.6 g of 2-amino-4-phenylthiazole are dissolved in 100 ml of tetrahydrofuran, the resulting solution is cooled to approximately 15° C. and 17.5 g of acetylene dicarboxylic acid diethyl ester are slowly added to it with stirring at that temperature. The mixture is left standing for 3 days, after which the crystals formed are filtered off the quantity of which was increased by concentrating the mother liquor to approximately half its original volume and recrystallized from ethanol. 3-Phenyl-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester is thus obtained in a yield of 16.9 g, corresponding to 56.3% of the theoretical.

Workup

  1. waitThe mixture is left
  2. customafter which the crystals formed
  3. filtrationare filtered off the quantity of which
  4. temperaturewas increased
  5. concentrationby concentrating the mother liquor to approximately half its original volume
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6db19717424143e3b444dbd4e8f17f68
Source dataset
uspto-grants-1980_12
Patent number
US04237136

Reaction notes

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