Potassium Carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate

HRID 1021383노트

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HRID 1021383 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][CH:5]2[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+].[Cl:23][C:24]1[CH:44]=[CH:43][C:27]([CH2:28][CH2:29][NH:30][C:31](=[O:42])[C:32]2[CH:37]=[CH:36][C:35](Cl)=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[CH:26][CH:25]=1>CS(C)=O>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][CH2:29][NH:30][C:31]([C:32]2[CH:37]=[CH:36][C:35]([O:12][C:11]3[CH:10]=[C:9]4[C:4]([CH:5]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:7][O:8]4)=[CH:3][C:2]=3[Cl:1])=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[O:42])=[CH:43][CH:44]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 4810824N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamideHCID 67080353Methyl 6-chloro-7-hydroxychroman-4-carboxylate

생성물 1

HCID 67080437Methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate수율 26.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
62 °C

실험 절차

Methyl 6-chloro-7-hydroxychroman-4-carboxylate (100 mg, 0.412 mmol) (Preparation 4, substituting methanol for ethanol in Step C) was diluted with DMSO (1 mL) followed by the addition of K2CO3 (68.3 mg, 0.495 mmol) and N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamide (140 mg, 0.412 mmol). The reaction was heated to 62° C. and stirred for 3 hours. The reaction was cooled, loaded directly onto silica gel and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate (60 mg, 26.7% yield).

후처리

  1. temperatureThe reaction was cooled
  2. washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

출처 및 근거

ORD 기록
ord-ae5673de7aac404c85f0a9daf7a4d920
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716498B2

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