Triethylamine → 3-Diethylthiocarbamoyloxy-2-fluoropyridine

HRID 52133

Reaction equation

HRID 52133 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]([CH2:14][CH3:15])[C:11](Cl)=[S:12])[CH3:9].[F:16][C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:8]([N:10]([CH2:14][CH3:15])[C:11]([O:23][C:22]1[C:17]([F:16])=[N:18][CH:19]=[CH:20][CH:21]=1)=[S:12])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66607Diethylthiocarbamoyl chlorideHCID 27627852-Fluoro-3-hydroxypyridine

Product 1

HCID 199632423-Diethylthiocarbamoyloxy-2-fluoropyridineYield 86.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

36.2 g (358 mmol) of triethylamine and 54.3 g (358 mmol) of diethylthiocarbamoyl chloride are added in succession to a suspension of 36.7 g (325 mmol) of 2-fluoro-3-hydroxypyridine in 150 ml of toluene at room temperature, and the reaction mixture is heated at 75° C. After the reaction mixture has been stirred at this temperature for 1 hour, it is cooled to room temperature, diluted with ethyl acetate, washed 3 times with water, dried over Na2SO4 and concentrated in vacuo at 60° C.; 80 g of brown oil which, after recrystallization from Et2O/hexane, gave 64.2 g (86%) of brown crystals of m.p. 52°-54° C.

Workup

  1. temperatureit is cooled to room temperature
  2. washwashed 3 times with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo at 60° C.
  5. custom80 g of brown oil which, after recrystallization from Et2O/hexane

Sources & evidence

ORD record
ord-685f9a15481e484ea0fd2be8b7a312fa
Source dataset
uspto-grants-1997_04
Patent number
US05616590

Linked notes

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