Phosphorus oxychloride → 4-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridine

반응식

[I:1][C:2]1[C:3]2[S:11][C:10]([CH3:12])=[N:9][C:4]=2[C:5](=O)[NH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[C:4]2[N:9]=[C:10]([CH3:12])[S:11][C:3]=2[C:2]([I:1])=[CH:7][N:6]=1

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 685382577-Iodo-2-methyl-5H-thiazolo[4,5-c]pyridin-4-one

생성물 1

HCID 768504784-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridine

실험 절차

7-Iodo-2-methyl-5H-thiazolo[4,5-c]pyridin-4-one (880 mg, 3.01 mmol) was suspended in POCl3 (8.25 ml, 90.4 mmol) and refluxed for 4 hrs. The black reaction mixture was evaporated and poured as a dichloromethane solution in ice water. The aqueous layer was neutralized with solid NaHCO3 to pH 7 and extracted three times with dichloromethane. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/methanol 100:0->95:5 gradient). The desired product was obtained as a light yellow solid (280 mg, 30%), MS: m/e=311.0 (M+H+).

후처리

temperaturerefluxed for 4 hrs
customThe black reaction mixture
customwas evaporated
additionpoured as a dichloromethane solution in ice water
extractionextracted three times with dichloromethane
dry with materialThe combined organic extracts were dried with magnesium sulfate
filtrationfiltered
customevaporated
customThe crude product was purified by chromatography on silica gel (dichloromethane/methanol 100:0->95:5 gradient)

출처 및 근거

ORD 기록: ord-b2045eb1d6a540f7a59604198367d3ce
출처 데이터셋: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07659401B2

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