Trimethyl orthoformate → HCID 67268034, compound

HRID 602772Notes

Reaction equation

[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[CH:20](OC)(OC)OC>>[C:1]1([S:7]([CH2:10][C:11]2[O:12][CH:20]=[N:14][N:13]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 9005Trimethyl orthoformate

HCID 24813Phosphorus oxychloride

HCID 11378890Benzenesulfonyl-acetic acid hydrazide

Product 1

HCID 67268034HCID 67268034, compoundYield 52%

Procedure

To 1.73 g (8.07 mmol) of benzenesulfonyl-acetic acid hydrazide were added 20 mL of trimethyl orthoformate and 1.26 g (8.07 mmol, 1 eq) of phosphorous oxychloride. The reaction mixture was stirred one hour at RT, and concentrated under reduced pressure. Column chromatography on silica gel with EtOAc/hexane 2:1 yielded 930 mg (52%) of 2-benzenesulfonylmethyl-[1,3,4]oxadiazole as a white solid, MS: 225 (MH+).

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-bd068a0f5fb349a29b4022a55a4afdea
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

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