Diisopropylethylamine → HCID 178425042, compound

HRID 853001Notes

Reaction equation

HRID 853001 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[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]=[CH:8][CH:7]=[C:6]([CH3:10])[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 5217992-Chloro-6-methylbenzylamineHCID 1201546Rhodanine

Product 1

HCID 178425042HCID 178425042, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-6-methyl-benzylamine (650 mg, 4.2 mmol) and Rhodanine (559 mg, 4.2 mmol) in acetonitrile (25 mL) was added DIPEA (1.74 mL, 10 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (1.22 g, 4.5 mmol) was added in one portion. 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 the solution was stored in the refrigerator overnight. Then, the solids were collected by filtration and washed with ethyl acetate. After drying in air, 305 mg (28.5% yield) of 2-(2-chloro-6-methyl-benzylamino)-thiazol-4-one was isolated as a white amorphous solid: EI-HRMS m/e calcd for C11H11ClN2OS (M+) 254.0281, found 254.0282.

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. customwas stored 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-d62fa8e3529c4a038a39217053304449
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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