(Chlorothio)formyl chloride → HCID 90418472, compound

HRID 2177182Notes

Reaction equation

HRID 2177182 reaction equation
[F:1][C:2]1([F:10])[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3]1.Cl[C:12]([S:14]Cl)=[O:13]>>[F:1][C:2]1([F:10])[CH2:6][CH2:5][CH:4]([C:7]2[O:8][C:12](=[O:13])[S:14][N:9]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 90418630HCID 90418630, compound

Product 1

HCID 90418472HCID 90418472, compound

Conditions

Temperature
100 °C

Procedure

Into a 100-mL round-bottom flask, was placed 3,3-difluorocyclopentane-1-carboxamide (1.5 g, 10.06 mmol, 1.00 equiv), tol (30 mL), chloro(chlorosulfanyl)methanone (2.6 g, 19.85 mmol, 1.97 equiv). The resulting solution was stirred for overnight at 100° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10-1/30). This resulted in 300 mg of 5-(3,3-difluorocyclopentyl)-2H-1,3,4-oxathiazol-2-one as brown oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 300 mg of 5-(3,3-difluorocyclopentyl)-2H-1,3,4-oxathiazol-2-one as brown oil

Sources & evidence

ORD record
ord-851777990b5841ea909de43099c8898b
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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