1,3-Dichlorobenzene → HCID 90418402, compound

HRID 2177183Notes

Reaction equation

HRID 2177183 reaction equation
[F:1][C:2]1([F:13])[CH2:6][CH2:5][CH:4]([C:7]2OC(=O)[S:9][N:8]=2)[CH2:3]1.ClC1C=CC=C(Cl)C=1.[F:22][C:23]([F:32])([F:31])[C:24]#[C:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[F:1][C:2]1([F:13])[CH2:6][CH2:5][CH:4]([C:7]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([C:23]([F:31])([F:32])[F:22])[S:9][N:8]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 109431,3-DichlorobenzeneHCID 3597254Ethyl 4,4,4-trifluoro-2-butynoateHCID 90418472HCID 90418472, compound

Product 1

HCID 90418402HCID 90418402, compound

Conditions

Temperature
160 °C

Procedure

Into a 10-mL sealed tube, was placed 5-(3,3-difluorocyclopentyl)-2H-1,3,4-oxathiazol-2-one (300 mg, 1.45 mmol, 1.00 equiv), 1,3-dichlorobenzene (2 mL), ethyl 4,4,4-trifluorobut-2-ynoate (481 mg, 2.90 mmol, 2.00 equiv). The resulting solution was stirred overnight at 160° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/30). This resulted in 200 mg of ethyl 3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate as brown oil.

Workup

  1. customInto a 10-mL sealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 200 mg of ethyl 3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate as brown oil

Sources & evidence

ORD record
ord-465dc457d6e547a487f9f4fc8adfd6b7
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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