Diisopropylethylamine → HCID 178516940, compound

HRID 853005Notes

Reaction equation

HRID 853005 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[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>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:12]1[S:11][CH2:17][C:15](=[O:16])[N:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1399092-Chloro-4-fluorobenzylamineHCID 1201546Rhodanine

Product 1

HCID 178516940HCID 178516940, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-4-fluoro-benzylamine (4.5 g, 28.19 mmol) and Rhodanine (3.75 g, 28.2 mmol) in acetonitrile (170 mL) was added DIPEA (9.82 mL, 56.4 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (8.42 g, 31.02 mmol) was added in two portions within 10 min. 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 acetonitrile (1.0 L) and ethyl acetate (500 mL). The combined filtrates were removed under the vacuum and the crude residue was dissolved in ethyl acetate (150 mL) and washed with water and brine solution. After drying over magnesium sulfate, the filtrate was removed under the vacuum and the residue was dissolved in ethyl acetate (50 mL) at hot condition. After cooling in the refrigerator overnight, the solids were collected by filtration and washed with hexanes. After drying in air, 1.2 g (16.5% yield) of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one was isolated as a white amorphous solid: EI-HRMS m/e calcd for C10H8FN2OS2 (M+) 258.0030, found 258.0027.

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 acetonitrile (1.0 L) and ethyl acetate (500 mL)
  5. customThe combined filtrates were removed under the vacuum
  6. dissolutionthe crude residue was dissolved in ethyl acetate (150 mL)
  7. washwashed with water and brine solution
  8. dry with materialAfter drying over magnesium sulfate
  9. customthe filtrate was removed under the vacuum
  10. dissolutionthe residue was dissolved in ethyl acetate (50 mL) at hot condition
  11. temperatureAfter cooling in the refrigerator overnight
  12. filtrationthe solids were collected by filtration
  13. washwashed with hexanes
  14. customAfter drying in air

Sources & evidence

ORD record
ord-574ba6643c4240908437a799bd0fab8d
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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