1,3-Dichlorobenzene → HCID 90418225, compound

HRID 2177204Notes

Reaction equation

HRID 2177204 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:25])([CH3:24])[C:17]#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].ClC1C=CC=C(Cl)C=1>>[F:15][C:16]([C:17]1[S:11][N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])([F:25])[CH3:24]

Participants

4

Reactant 3

HCID 109431,3-DichlorobenzeneHCID 71290725HCID 71290725, compoundHCID 90417940HCID 90417940, compound

Product 1

HCID 90418225HCID 90418225, compound

Conditions

Temperature
150 °C

Procedure

Into a 10-mL sealed tube, was placed 5-(4-ethylphenyl)-2H-1,3,4-oxathiazol-2-one (227 mg, 1.10 mmol, 1.00 equiv), ethyl 4,4-difluoropent-2-ynoate (357 mg, 2.20 mmol, 2.01 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 (1:10). This resulted in 0.191 g (54%) of ethyl 5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazole-4-carboxylate as orange oil.

Workup

  1. customInto a 10-mL sealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 0.191 g (54%) of ethyl 5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazole-4-carboxylate as orange oil

Sources & evidence

ORD record
ord-71b1a8adf84d41b080bd878cd8af3bbe
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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