Ethanol → HCID 14672730, compound

HRID 619880Notes

Reaction equation

HRID 619880 reaction equation
C(O)C.Cl[C:5]1[S:6][C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>O>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:5]1[S:6][C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 104392-AminopyridineHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 14672730HCID 14672730, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A reaction vessel was charged with 100 ml ethanol, 13.0 g (50 mmol) ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate and 9.41 g (100 mmol) 2-aminopyridine. The reaction mixture was heated at a temperature of about 80° C. for 80 hours. The mixture was cooled to room temperature. This mixture was diluted with water and extracted three times with ethyl ether. The combined ether extracts were washed with large amounts of water, dried over magnesium sulfate, and concentrated under reduced pressure to give 19.1 g of a brown, wet, solid material. This material was recrystallized from a 1:1 ethanol:water solution over a 36-hour period. The recrystallized material was suction filtered to give 3.9 g of a dark brown solid material which was triturated in warm hexane to give 2.3 g of brown solid product (m.p. 07°-111° C.) identified in Table I.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted three times with ethyl ether
  3. washThe combined ether extracts were washed with large amounts of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give 19.1 g of a brown, wet, solid material
  7. customThis material was recrystallized from a 1:1 ethanol
  8. waitwater solution over a 36-hour period
  9. filtrationfiltered

Sources & evidence

ORD record
ord-4db46aa6f5db46a2acb881a0de167de1
Source dataset
uspto-grants-1989_04
Patent number
US04818270

Reaction notes

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