Sodium Iodide → HCID 42637597, compound

HRID 1816179Notes

Reaction equation

HRID 1816179 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:33][O:32][C:30](=[O:31])[C:29]1[CH:34]=[CH:35][C:26]([CH2:25][N:13]([C:10]2[S:11][CH:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][CH:15]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 22496401HCID 22496401, compound

Product 1

HCID 42637597HCID 42637597, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

[4-(4-Chlorophenyl)thiazol-2-yl]-(4-trifluoromethylphenyl)amine (0.335 mg; 0.95 mmol) was dissolved in acetonitril (4 ml) and methyl 4-(bromomethyl)benzoate (238 mg; 1.04 mmol), potassium carbonate (195 mg; 1.41 mmol) and sodium iodide (212 mg; 1.41 mmol) were added. The reaction mixture was heated to 60° C. for 3 days, then filtered while still hot. The solvent was removed by rotary evaporation, then the residue was dissolved in ethyl acetate (50 ml) and washed with water (50 ml) and brine (50 ml). The organic phase was dried with sodium sulphate, and taken to dryness by rotary evaporation. The residue was striped once with acetonitril to give pure 4-{[[4-(4-chlorophenyl)thiazol-2-yl]-(4-trifluoromethylphenyl)amino]methyl}benzoic acid methyl ester as an oil. Yield; 454 mg (96%).

Workup

  1. filtrationfiltered while still hot
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  4. washwashed with water (50 ml) and brine (50 ml)
  5. dry with materialThe organic phase was dried with sodium sulphate
  6. customtaken to dryness by rotary evaporation

Sources & evidence

ORD record
ord-fb2ab84615dd4d65a33402d3a4e3d646
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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