Triethylamine → HCID 23144355, compound

HRID 1361770Notes

Reaction equation

HRID 1361770 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[NH2:16][C:17]1[S:18][C:19]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[C:20]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:16][C:17]2[S:18][C:19]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[C:20]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[O:9])=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 225994-(Bromomethyl)benzoic acidHCID 24386Thionyl ChlorideHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole

Product 1

HCID 23144355HCID 23144355, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromomethylbenzoic acid (2.24 g, 10.4 mmol) was dissolved in toluene (80 mL), and thionyl chloride (7.59 mL, 104 mmol) was added thereto, followed by stirring under heating and reflux for 6 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in THF (50 mL), and 2-amino-4-(2-furyl)-5-morpholinothiazole (2.00 g, 7.97 mmol) obtained in Step 1 of Example 29, triethylamine (1.67 mL, 12.0 mmol) and N,N-dimethylaminopyridine (97.6 mg, 0.800 mmol) were added thereto, followed by stirring under heating and reflux for 1 hour. The reaction mixture was allowed to cool down to room temperature, and then a 10% aqueous solution of sodium carbonate was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:ethyl acetate=9:1) to afford the entitled Compound 59 (3.29 g, 92%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 6 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in THF (50 mL)
  5. stirringby stirring
  6. temperatureunder heating
  7. temperaturereflux for 1 hour
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled away under reduced pressure
  12. customThe resulting residue was purified through silica gel column chromatography (chloroform:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-62cc25d8e7514f7a957420996aa1fa6e
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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