(Chlorothio)formyl chloride → Ethyl 2,3-dihydro-2-oxo-4-phenyl-5-thiazolecarboxylate

HRID 1156593Notes

Reaction equation

HRID 1156593 reaction equation
[NH2:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[C:16]([S:18]Cl)=[O:17]>ClC1C=CC=CC=1>[O:17]=[C:16]1[NH:1][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[S:18]1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 312934Ethyl 3-amino-3-phenylprop-2-enoate

Product 1

HCID 13041815Ethyl 2,3-dihydro-2-oxo-4-phenyl-5-thiazolecarboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 20.0 g (0.105 mole) of ethyl β-amino-cinnamate in 40 ml. of chlorobenzene under ice cooling was added a solution of 11.6 g (0.112 mole) of chorocarbonylsulfenyl chloride in 10 ml. of chlorobenzene. The reaction mixture was heated at 110° C. for 2 hours, cooled to triturated with petroleum ether. The precipitate was heated with hot benzene, cooled and filtered to give 14.4 g (55%) of ethyl 2,3-dihydro-2-oxo-4-phenyl-5-thiazolecarboxylate as yellow needles. A mixture of 3.0 g (0.012 mole) of ethyl 2,3-dihydro-2-oxo-4-phenyl-5-thiazolecarboxylate and 14 ml. of phosphorus oxychloride was held at reflux for 24 hours and cooled. The reaction mixture was poured into ice water. The solid precipitate was extracted into ether. The ether solution was dried and concentrated under reduced pressure. The residue was recrystallized from hexane to give 2.2 g (68%) of ethyl 2-chloro-4-phenyl-5-thiazolecarboxylate, m.p. 56°-57° C.

Workup

  1. temperaturecooled
  2. customto triturated with petroleum ether
  3. temperatureThe precipitate was heated with hot benzene
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ebb93e671a914eccbdecaa4530183450
Source dataset
uspto-grants-1982_06
Patent number
US04336389

Reaction notes

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