Diisopropylethylamine → HCID 178429647, compound

HRID 1783637Notes

Reaction equation

HRID 1783637 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][NH2:8].[S:9]1[CH2:15][C:13](=[O:14])[NH:12][C:10]1=S.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][NH:8][C:10]1[S:9][CH2:15][C:13](=[O:14])[N:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1201546RhodanineHCID 2798756(3-Methylthiophen-2-yl)methanamine

Product 1

HCID 178429647HCID 178429647, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methyl-thiophen-2-ylmethylamine (700 mg, 5.5 mmol) and rhodanine (732 mg, 5.5 mmol) in acetonitrile (30 mL) was added diisopropylethylamine (DIEA) (1.91 mL, 11 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (1.52 g, 5.6 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 acetonitrile (200 mL) and ethyl acetate (250 mL). The filtrates were removed under the vacuum and the crude residue was dissolved in dichloromethane (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 dichloromethane (10 mL) and diluted with hexanes (10 mL). After overnight storage in the refrigerator, the solids were collected by filtration and washed with dichloromethane. After drying in air, 390 mg (31.5% yield) of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one was isolated as a light yellow amorphous solid: EI-HRMS m/e calcd for C9H10N2OS2 (M+) 226.0235, found 226.0232.

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 (200 mL) and ethyl acetate (250 mL)
  5. customThe filtrates were removed under the vacuum
  6. dissolutionthe crude residue was dissolved in dichloromethane (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 dichloromethane (10 mL)
  11. additiondiluted with hexanes (10 mL)
  12. waitAfter overnight storage in the refrigerator
  13. filtrationthe solids were collected by filtration
  14. washwashed with dichloromethane
  15. customAfter drying in air

Sources & evidence

ORD record
ord-aa6831f0a5fb436195e70ba8fb5525d5
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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