Ethyl orthoformate → Methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate

HRID 1276132Notes

Reaction equation

HRID 1276132 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([NH:14][NH2:15])=[O:13])=[C:10]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:20](OCC)(OCC)OCC>>[Cl:1][C:2]1[C:11]([C:12]2[O:13][CH:20]=[N:15][N:14]=2)=[C:10]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 22114944Methyl 2-chloro-3-hydrazinocarbonyl-4-methylsulfonylbenzoate

Product 1

HCID 22114931Methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate

Procedure

1.16 g (3.8 mmol) of methyl 2-chloro-3-hydrazinocarbonyl-4-methylsulfonylbenzoate and 10 ml of triethyl orthoformate were heated under reflux for 6 hours. The precipitate that had formed was filtered off with suction, washed with n-hexane and subsequently taken up in 20 ml of toluene. After the addition of p-toluenesulfonic acid, the mixture was heated at reflux for 3 hours and then cooled, washed with water, dried and concentrated. 0.62 g (52% of thoery) of methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate was obtained.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe precipitate that had formed
  3. filtrationwas filtered off with suction
  4. washwashed with n-hexane
  5. additionAfter the addition of p-toluenesulfonic acid
  6. temperaturethe mixture was heated
  7. temperatureat reflux for 3 hours
  8. temperaturecooled
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f6d57a8905ae405988b3e9f4b0b87af4
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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