Dabco → HCID 13753213, compound

HRID 1732154Notes

Reaction equation

HRID 1732154 reaction equation
N12CCN(CC1)CC2.[CH2:9]([N:11]=[C:12]=[S:13])[CH3:10].[F:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][C:20]2[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][OH:27])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][C:20]2[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][O:27][C:12](=[S:13])[NH:11][CH2:9][CH3:10])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 10966Ethyl isothiocyanateHCID 13753176HCID 13753176, compound

Product 1

HCID 13753213HCID 13753213, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

50 mg of 1,4-diazabicyclo(2,2,2)octane and 0.9 g of ethyl isothiocyanate are added to a solution of 2.3 g of 2-[p-(p-fluorophenoxy)phenoxy]-ethanol in 10 ml of pyridine. The mixture is then allowed to stir at 80° C. for 16 hours. The cooled mixture is poured into 50 ml of ice/water and extracted three times with 80 ml of ethyl acetate each time. The extracts are washed twice with 50 ml of water each time and with 50 ml of sodium chloride solution. The extracts are dried over anhydrous sodium sulfate and evaporated. The residue is purified chromatography on silica gel with n-hexane/ethyl acetate (2:1) to yield pure [2-[p-(p-fluorophenoxy)phenoxy]-ethyl]N-ethylthiocarbamate; m.p. 73°-75° C.

Workup

  1. extractionextracted three times with 80 ml of ethyl acetate each time
  2. washThe extracts are washed twice with 50 ml of water each time
  3. dry with materialThe extracts are dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue is purified chromatography on silica gel with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-05ceffc3e0b54e6f9ab6e7d38d13c0ed
Source dataset
uspto-grants-1986_11
Patent number
US04625048

Reaction notes

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