Triethylamine → HCID 67546557, compound

HRID 2356736Notes

Reaction equation

HRID 2356736 reaction equation
NC[C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:6][C:7]=1[C:8]1[CH:12]=[CH:11][S:10][CH:9]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([N:27](CC)CC)C.[Cl-].[NH4+]>ClCCl>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[O:6][C:7]([C:8]3[CH:12]=[CH:11][S:10][CH:9]=3)=[C:3]([NH:27][S:21]([CH3:20])(=[O:23])=[O:22])[N:4]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 67546555HCID 67546555, compound

Product 1

HCID 67546557HCID 67546557, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-aminomethyl-2-(4-fluorophenyl)-5-(3-thienyl)oxazole (110 mg) in dichloromethane (5 ml) were successively added dropwise under acetone-ice cooling methanesulfonyl chloride (0.036 ml) and triethylamine (0.15 ml) The reaction mixture was stirred at 0° C. for one hour, and further stirred at room temperature for 2 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution and extracted with chloroform. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent: chloroform:methanol=100:0→95:5) to obtain a crude product of N-[2-(4-fluorophenyl)-5-(3-thienyl)oxazol-4-yl]-methanesulfonamide (140 mg).

Workup

  1. additionwere successively added dropwise under acetone-ice
  2. stirringfurther stirred at room temperature for 2 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent: chloroform:methanol=100:0→95:5)

Sources & evidence

ORD record
ord-80ed0c0ec84649bd807ea8f9f00ac51e
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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