Phosphorus oxychloride → HCID 25234176, compound

HRID 1665009Notes

Reaction equation

[CH2:1]([N:8]([CH2:22][C:23]([NH:25][NH:26][C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=1)=[O:24])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>>[CH2:1]([N:8]([CH2:22][C:23]1[O:24][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=2)=[N:26][N:25]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])(=[O:10])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 67441840HCID 67441840, compound

Product 1

HCID 25234176HCID 25234176, compoundYield 68.8%

Conditions

Temperature: 110 °C

Procedure

A mixture of N-benzyl-N-{2-[N′-(3-methanesulfonyl-benzoyl)-hydrazino]-2-oxo-ethyl}-2-trifluoromethyl-benzenesulfonamide (111 mg) and phosphorus oxychloride (1.5 g) was stirred for 18 h at 110° C. and then was concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:1 to ethyl acetate) to give N-benzyl-N-[5-(3-methanesulfonyl-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (74 mg) as a colorless foam. MS: 552.3 ([M+H]+)

Workup

concentrationwas concentrated under reduced pressure
customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:1 to ethyl acetate)

Sources & evidence

ORD record: ord-05c6932addcf4883a7d450b0a10f9b64
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039493B2

Reaction notes

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