5-Fluoro-o-tolyl Isothiocyanate → Methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate

HRID 1372638Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=S)[CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[OH:24]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]2[O:24][C:14]3[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=3[N:12]=2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In methanol (50 ml), 5-fluoro-2-methylphenyl isothiocyanate (2.00 g, 12.0 mmol) was added to methyl 4-amino-3-hydroxyphenylacetate (2.17 g, 12.0 mmol) at room temperature. After stirring for 27 hours, mercuric oxide (yellow) (3.12 g, 14.4 mmol) was added to the reaction mixture and the resulting mixture was heated at 70° C. for 4 hours. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was washed with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions, methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate (1.73 g, 46%) was obtained as a pale brown oil.

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered through Celite
washThe filtrate was washed with methanol
distillationThe filtrate was distilled under reduced pressure
customto remove the solvent
customThe residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions

Sources & evidence

ORD record: ord-5f136369040e47248e568276b8621d6b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

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