Sulfuryl chloride → Ethyl 3-(2-chloro-4-fluorophenyl)-3-oxopropanoate

HRID 1660561Notes

Reaction equation

HRID 1660561 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:19])(=O)=O>C(Cl)(Cl)Cl>[Cl:19][C:4]1[CH:3]=[C:2]([F:1])[CH:15]=[CH:14][C:5]=1[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Product 1

HCID 54191286Ethyl 3-(2-chloro-4-fluorophenyl)-3-oxopropanoateYield 88.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 10.5 g (0.05 mole) of ethyl p-fluorobenzoylacetate, 6.7 g (0.05 mole) of sulfuryl chloride and 30 ml. of chloroform was held at reflux for 18 hours and cooled. The chloroform solution was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was distilled to give 10.8 g (88%) of ethyl 2-chloro-(p-fluoro)-benzoylacetate as an oil. A mixture of 10.8 g (0.441 mole) of ethyl 2-chloro-(p-fluoro)-benzoylacetate, 3.36 g (0.0441 mole) of thiourea, 20 ml. of water and 10 ml. of ethanol was held at reflux for 3 hours. Ethanol was removed under reduced pressure. The residue was made basic with saturated sodium bicarbonate. The solid was filtered, washed with water and recrystallized from ethanol to give 8.9 g (76%) of ethyl 2-amino-4-(p-fluorophenyl)-5-thiazolecarboxylate as white prisms, m.p. 205°-208° C.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. washThe chloroform solution was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-9f3494f8aebb43b9be54d9ff970ec623
Source dataset
uspto-grants-1981_12
Patent number
US04308391

Reaction notes

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