Tetrahydrofuran → HCID 66868556, compound

HRID 1909850Notes

Reaction equation

HRID 1909850 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1COCC1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=S)=[CH:21][CH:20]=1>[Cu](I)I.C(N(CC)CC)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[O:12][C:3]3[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=3[N:1]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 164804-Chlorophenyl isothiocyanateHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Product 1

HCID 66868556HCID 66868556, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Procedure

To a mixture of methyl 3-amino-2-hydroxybenzoate (700 mg) and THF (21 mL) was added 4-chlorophenylisothiocyanate (717 mg), followed by stirring at room temperature overnight. To the reaction mixture were sequentially added copper iodide (0.87 g) and triethylamine (641 μL), followed by stirring at 60° C. overnight. The reaction mixture was concentrated under reduced pressure and methanol was added thereto, the mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (20 mL), the insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and then triturated with n-hexane-ethyl acetate (10:1, 11 mL) to obtain methyl 2-[(4-chlorophenyl)amino]-1,3-benzoxazole-7-carboxylate (270 mg) as a pale yellow solid.

Workup

  1. stirringby stirring at 60° C. overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure and methanol
  3. additionwas added
  4. filtrationthe mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate (20 mL)
  7. customthe insoluble materials were removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)
  10. customtriturated with n-hexane-ethyl acetate (10:1, 11 mL)

Sources & evidence

ORD record
ord-19ed099e7a704ed8885dd6aad7a2b7f9
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

Loading…