2-Amino-3,4,6-trifluorobenzenethiol → Methyl 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]phenylacetate

HRID 1940604Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[SH:11].[CH3:12][O:13][C:14]([CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][C:24](Cl)=O)[CH:20]=[CH:21][CH:22]=1)=[O:15]>CN1CCCC1=O.O>[F:8][C:7]1[C:2]2[N:1]=[C:24]([CH2:23][C:19]3[CH:18]=[C:17]([CH2:16][C:14]([O:13][CH3:12])=[O:15])[CH:22]=[CH:21][CH:20]=3)[S:11][C:3]=2[C:4]([F:10])=[CH:5][C:6]=1[F:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of monomethyl 1,3-phenylene diacetate (531 mg, 2.6 mmol) in benzene (5 ml) was gradually added thionyl chloride (607 mg, 5.2 mmol). The mixture was heated to reflux for 2 hours. An excess of thionyl chloride was then distilled off in vacuo leaving 3-methoxycarbonylmethylphenylacetyl chloride. 2-Amino-3,4,6-trifluorothiophenol (507 mg, 2.8 mmol) was dissolved in N-methylpyrrolidone (NMP, 5 ml) under a nitrogen stream. To the resultant solution was gradually added the product 3-methoxycarbonylmethylphenylacetyl chloride thus obtained and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried and then evaporated to yield a residue, which was purified on a silica gel column to give methyl 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]phenylacetate (267 mg, 27%) as an oil.

Workup

customthus obtained
temperatureAfter cooling
extractionextracted with ethyl acetate
customThe organic layer was dried
customevaporated
customto yield a residue, which
customwas purified on a silica gel column

Sources & evidence

ORD record: ord-732132c109c344a5a72736317f8966c5
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05700819

Reaction notes

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