1,3-Dichlorobenzene → HCID 90418223, compound
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2OC(=O)[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[F:15][C:16]([F:28])([C:24]([F:27])([F:26])[F:25])[C:17]#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].ClC1C=CC=C(Cl)C=1>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([C:16]([F:28])([F:15])[C:24]([F:25])([F:26])[F:27])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2]Participants
4
Conditions
- Temperature
- 150 °C
Procedure
Into a 10-mL sealed tube, was placed 5-(4-ethylphenyl)-2H-1,3,4-oxathiazol-2-one (155 mg, 0.75 mmol, 1.00 equiv), ethyl 4,4,5,5,5-pentafluoropent-2-ynoate (250 mg, 1.16 mmol, 1.55 equiv), 1,3-dichlorobenzene (3 mL). The resulting solution was stirred for 16 h at 150° C. in an oil bath. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:19). The resulted in a mixture of the product 0.192 g as the yellow oil. Mass spectrum (ESI, m/z): Calcd. for C16H14F5NO2S, 380.3 (M+H). found 380.3.
Workup
- customInto a 10-mL sealed tube
- concentrationThe resulting mixture was concentrated under vacuum
Sources & evidence
- ORD record
- ord-a77070ba095440a3bca47d00f4b5f709
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067898B1
Reaction notes
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