Cesium carbonate → HCID 21949461, compound

HRID 2215099Notes

Reaction equation

HRID 2215099 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Cl[CH2:14][C:15]1[S:19][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O>[CH3:30][C:16]1[N:17]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)[S:19][C:15]=1[CH2:14][S:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 219494996-Sulfanyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 21949461HCID 21949461, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-mercapto-3,4-dihydro-2H-naphthalen-1-one (3.5 g, 20 mmol) in acetonitrile (100 mL), under nitrogen atmosphere, was added %-chloromethyl-4-methyl-2-(4-trifluoromethylphenyl)thiazole (5.7 g, 20 mmol) followed by cesium carbonate (6.4 g, 20 mmol). The resulting mixture was stirred 16 h, diluted with water (100 mL). The precipitate was collected by filtration, dried, dissolved in EtOAc, and filtered through a plug of silica gel. The filtrate was concentrated under vacuum and the residue purified by recrystallization in iso-propanol to give 5.21 g (61%) of cream colored crystals. (mp 123–124° C.) Analyzed for C22H18F3NOS2: Calcd: C, 60.95%; H, 4.19%; N, 3.23%; Found: C, 60.79%; H, 4.09%; N, 3.09%.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried
  3. dissolutiondissolved in EtOAc
  4. filtrationfiltered through a plug of silica gel
  5. concentrationThe filtrate was concentrated under vacuum
  6. customthe residue purified by recrystallization in iso-propanol
  7. customto give 5.21 g (61%) of cream colored crystals

Sources & evidence

ORD record
ord-939305db8937402ba2300553d39a5143
Source dataset
uspto-grants-2006_09
Patent number
US07109222B2

Reaction notes

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