Diisopropylethylamine → 2-[(3-Fluorophenyl)-ethylamino]-thiazol-4-one

HRID 853012Notes

Reaction equation

HRID 853012 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[S:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=S.CCN(C(C)C)C(C)C>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:9][CH3:10])[C:12]2[S:11][CH2:17][C:15](=[O:16])[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1201546RhodanineHCID 11062466N-ethyl-3-fluoroaniline

Product 1

HCID 688188702-[(3-Fluorophenyl)-ethylamino]-thiazol-4-oneYield 76.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3-fluorophenyl)-ethylamine (3.06 g, 22 mmol) and rhodanine (2.66 g, 20 mmol) in acetonitrile (70 mL) was added DIEA (7.66 mL, 44 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (5.97 g, 22 mmol) was added in two portions. After addition, the suspension was allowed to warm to room temperature and stirred for 3 days. The resulting black solids were filtered through a plug of celite and washed with dichloromethane (500 mL) and methanol (250 mL). The combined solvents were removed under the vacuum and the crude residue was dissolved in ethyl acetate (25 mL) at hot condition and stored in the refrigerator overnight. Then, the solids were collected by filtration and washed with ethyl acetate. After drying in air, 3.65 g (76.6% yield) of 2-[(3-fluorophenyl)-ethylamino]-thiazol-4-one was isolated as a white amorphous solid: HRES(+) m/e calcd for C11H11FN2OS (M+H)+239.0649, found 239.0647.

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. filtrationThe resulting black solids were filtered through a plug of celite
  4. washwashed with dichloromethane (500 mL) and methanol (250 mL)
  5. customThe combined solvents were removed under the vacuum
  6. dissolutionthe crude residue was dissolved in ethyl acetate (25 mL) at hot condition
  7. customstored in the refrigerator overnight
  8. filtrationThen, the solids were collected by filtration
  9. washwashed with ethyl acetate
  10. customAfter drying in air

Sources & evidence

ORD record
ord-542fa8fae4f14cdbac6e226fdc5731db
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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