Phenyl isocyanate → HCID 23372942, compound

HRID 1899705Notes

Reaction equation

[Li]CCCC.[CH3:6][C:7]1[C:11]([CH3:12])=[C:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:16])=[O:15])[O:9][N:8]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([NH:29][C:30]([C:22]2[C:17]([S:14]([NH:13][C:10]3[O:9][N:8]=[C:7]([CH3:6])[C:11]=3[CH3:12])(=[O:15])=[O:16])=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -78 °C

Procedure

nBuLi (1.8 ml, 2.34M) was slowly added to a solution of N-(3,4-dimethyl-5-isoxazolyl)pyridine-2-sulfonamide (500 mg, 2.0 mmol) in THF (14 ml) at -78° C. The mixture was stirred at -78° C. for 1 hour. Phenylisocyanate (3.55 mg, 2.9 mmol) was then added slowly and the mixture was allowed to warm room temperature. The reaction was quenched with H2O and the volatiles were removed under reduced pressure. The aqueous residue was extracted with EtOAc (2×50 ml). The aqueous layer was acidified with concenrated HCl to pH 4(~50 ml) and extracted with EtOH (2×50 ml). The combined organic layer was dried (MgSO4), filtered and evaporated to give a yellow oil, which was purified by HPLC to give an 88% yield with a m.p. of 199°-200° C.

Workup

temperatureto warm room temperature
customThe reaction was quenched with H2O
customthe volatiles were removed under reduced pressure
extractionThe aqueous residue was extracted with EtOAc (2×50 ml)
extractionextracted with EtOH (2×50 ml)
dry with materialThe combined organic layer was dried (MgSO4)
filtrationfiltered
customevaporated
customto give a yellow oil, which
customwas purified by HPLC
customto give an 88% yield with a m.p. of 199°-200° C.

Sources & evidence

ORD record: ord-0e7e223e44b74843b8395b86234c4fe2
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571821

Reaction notes

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