Diethylamine → HCID 20064731, compound
Reaction equation
O[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.P(Cl)(Cl)(Cl)=O.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>>[CH2:21]([N:23]([CH2:24][CH3:25])[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1)[CH3:22]Participants
Conditions
- Temperature
- 163 °C
Procedure
A reaction vessel was charged with 96.4 g (400 mmol) of ethyl 2-hydroxy-4-trifluoromethyl-5-thiazolecarboxylate and 117 g (766 mmol) of phosphorus oxychloride and then cooled in an ice bath. To the cooled mixture was added 40 g of diethylamine. The reaction mixture was heated at reflux at 163° C. with stirring for about 14 hours. Excess phosphorus oxychloride was removed under reduced pressure. The residue was poured into ice water and a solid precipitate was collected. The solid precipitate was dissolved in ethyl ether, washed with 5% sodium hydroxide, dried with calcium sulfate, and concentrated under reduced pressure to provide 50 g of residue. This residue was subjected to Kugelrohr distillation (100°-120° C. @ 0.5 mm Hg) to provide 3.5 g of a yellow liquid identified in Table I.
Workup
- temperaturecooled in an ice bath
- temperatureThe reaction mixture was heated
- customExcess phosphorus oxychloride was removed under reduced pressure
- additionThe residue was poured into ice water
- customa solid precipitate was collected
- dissolutionThe solid precipitate was dissolved in ethyl ether
- washwashed with 5% sodium hydroxide
- dry with materialdried with calcium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-59ac93a27c3b4c1dbf52494466069f9d
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05000775
Reaction notes
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