4,5-Dihydro-2-(methylthio)thiazole → HCID 21915255, compound

HRID 2117838Notes

Reaction equation

HRID 2117838 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.CS[C:21]1[S:22][CH2:23][CH2:24][N:25]=1>COCCO>[S:22]1[CH2:23][CH2:24][N:25]=[C:21]1[NH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 21915094HCID 21915094, compound

Product 1

HCID 21915255HCID 21915255, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-{4-[(E)-2-(4-aminophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (200 mg), 2-(methylsulfanyl)-4,5-dihydro-1,3-thiazole (103 mg), hydrochrolic acid (0.064 ml) and 2-methoxyethanol (2 ml) was stirred at 120° C. for 8 hours. The reaction mixture was concentrated in vacuo. The residue was purified by silica-gel flash column chromatography with hexane:ethyl acetate (3:1) as an eluent. The crystalline residue was collected and washed with ethyl acetate to give N-(4-{(E)-2-[4-(4,5-dihydro-1,3-thiazol-2-ylamino)phenyl]ethenyl}-1,3-thiazol-2-yl)acetamide (150 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by silica-gel flash column chromatography with hexane:ethyl acetate (3:1) as an eluent
  3. customThe crystalline residue was collected
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-9f7f90151af4436d8cdcb48c66cb8892
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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