Diisopropylethylamine → HCID 178516940, compound

HRID 1296799Notes

Reaction equation

HRID 1296799 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 solvents were removed under the vacuum and the crude residue was dissolved in ethyl acetate (150 mL) and washed with water (100 mL) and brine solution (100 mL). After drying over magnesium sulfate, the filtrate was removed under the vacuum and the residue was dissolved in ethyl acetate (50 mL). 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 solvents were removed under the vacuum
  6. dissolutionthe crude residue was dissolved in ethyl acetate (150 mL)
  7. washwashed with water (100 mL) and brine solution (100 mL)
  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)
  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-1f02a6257eb842e6a2b2d1e275b895bd
Source dataset
uspto-grants-2007_07
Patent number
US07247727B2

Reaction notes

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