Methanol → 3-Methoxy-3-(4-dimethylaminophenyl)phthalide

HRID 1789273노트

반응식

HRID 1789273 반응식
[CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.CO.N1CCCC[CH2:28]1>C(Cl)CCl>[CH3:28][O:10][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:20])[CH3:1])=[CH:8][CH:7]=2)[C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13](=[O:15])[O:14]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 889372-[4-(Dimethylamino)benzoyl]benzoic acid

생성물 1

HCID 159186993-Methoxy-3-(4-dimethylaminophenyl)phthalide

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Following a procedure similar to that described in Example 1 above, 4.5 g of 2-(4-dimethylaminophenyl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of piperidine at ambient temperature for approximately ten minutes to obtain 4.0 g of 3-methoxy-3-(4-dimethylaminophenyl)phthalide (Formula II: R0 =R=R1 =R2 =R5 =H; R4 =R4' =R5Y=CH3 ; X=O), a pale peach-colored solid which melted at 112.5° to 114.5° C. A significant infrared maximum appeared at 1773 cm-1 (C=O; s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Analysis by mass spectrum showed m/e peaks at 283 (M+) and 252 (M+ -OCH3). A toluene solution of the product spotted on an acidic clay-coated paper developed a yellow-colored image.

출처 및 근거

ORD 기록
ord-8f2a46ac08b540f895adb954e2d1b4c0
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04688059

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