Nitrogen → 2,2-dimethyl-6-cyano-3,4-dihydro-2H-1,3-benzoxazin-4-one

HRID 1087373노트

반응식

HRID 1087373 반응식
N1C=CC=CC1=[O:7].[H-].[Na+].N#N.[CH3:12][C:13]1([CH3:26])[N:18]=[C:17](Cl)[C:16]2[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:15]=2[O:14]1.C(C1C=CC(O)=C(C=1)C(N)=O)#N>CN(C=O)C.CC(C)=O>[CH3:12][C:13]1([CH3:26])[NH:18][C:17](=[O:7])[C:16]2[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:15]=2[O:14]1

참가 물질

8

반응물 5

HCID 947NitrogenHCID 88712-PyridoneHCID 24758Sodium hydrideHCID 147215875-Cyano-2-hydroxybenzamideHCID 147215882,2-dimethyl-4-chloro-6-cyano-2H-1,3-benzoxazine

생성물 1

HCID 108219722,2-dimethyl-6-cyano-3,4-dihydro-2H-1,3-benzoxazin-4-one

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

1.9 g of 1H-2-pyridone are added to a stirred slurry of 741 mg of NaH (80%) in 40 ml of dry DMF while passing N2 into the flask. After the mixture has been stirred for 0.5 hour, 2.2 g of 2,2-dimethyl-4-chloro-6-cyano-2H-1,3-benzoxazine ("IIa"; m.p. 127°-129°; obtainable by condensing 5-cyano-2-hydroxybenzamide with acetone to form 2,2-dimethyl-6-cyano-3,4-dihydro-2H-1,3-benzoxazin-4-one (m.p. 213°-216°) and subsequently reacting the product with POCl3 /PCl5) are added, and the mixture is stirred at 50° for a further 72 hours. Saturated NaCl solution is subsequently added, the mixture is extracted with ethyl acetate, the organic phase is washed with NaCl solution, dried over sodium sulfate and evaporated, and the residue is chromatographed on silica gel (ethyl acetate/petroleum ether). 2,2-Dimethyl-4-(2-pyridyl-oxy)-6-cyano-2H-1,3-benzoxazine ("A"; m.p. 115°- 116°) is obtained as the first fraction, and 2,2-dimethyl-4-(2-oxo-1,2-dihydropyridyl)-6-cyano-2H-1,3-benzoxazine ("B"; m.p. 158°-159°) as the second fraction.

출처 및 근거

ORD 기록
ord-f5508cfcc2b24faa9a0890c650fb9d9e
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036068

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