Methanol → HCID 58779094, compound

HRID 1372633Notes

Reaction equation

HRID 1372633 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([F:12])[C:3]=1[OH:13].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=S.[CH3:24]O>>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]1[O:13][C:3]2[C:4]([F:12])=[C:5]([CH2:8][C:9]([O:11][CH3:24])=[O:10])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 17859270HCID 17859270, compound

Product 1

HCID 58779094HCID 58779094, compoundYield 50%

Procedure

In methanol (50 ml) was dissolved 4-amino-2-fluoro-3-hydroxyphenylacetic acid (2.52 g, 12.7 mmol). At room temperature, 2-chlorophenyl isothiocyanate (1.99 ml, 12.7 mmol) was added to the resulting solution. After the resulting mixture was stirred at room temperature for 2.5 hours, mercuric oxide (yellow) (3.29 g, 15.2 mmol) was added thereto. The mixture was stirred further for 14 hours at 70° C. The reaction mixture was allowed to cool down to room temperature. The insoluble matter was filtered off through Celite under reduced pressure, followed by washing with methanol. From the filtrate, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (silica gel: 100 g, chloroform/ethyl acetate (30/1)), whereby from eluate fractions, methyl 2-(2-chlorophenyl)amino-7-fluoro-6-benzoxazolylacetate (2.12 g, 50%) was obtained as a pale pink solid.

Workup

  1. stirringThe mixture was stirred further for 14 hours at 70° C
  2. temperatureto cool down to room temperature
  3. filtrationThe insoluble matter was filtered off through Celite under reduced pressure
  4. washby washing with methanol
  5. distillationFrom the filtrate, the solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column (silica gel: 100 g, chloroform/ethyl acetate (30/1)), whereby from eluate fractions

Sources & evidence

ORD record
ord-7d912632a95c4e028062a38d2721503c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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