p-Toluenesulfonic acid → Methyl 10-methoxy-5H-dibenz[b,f]azepine-5-carboxylate

HRID 2216924노트

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HRID 2216924 반응식
[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[CH2:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4].[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC)(OC)OC>CO>[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([O:16][CH3:21])=[CH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 1134617110-Oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid methyl ester

생성물 1

HCID 11208289Methyl 10-methoxy-5H-dibenz[b,f]azepine-5-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
25 °C

실험 절차

Crude 10-Oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid methyl ester (22.3 g, 0.083 mol, 1 eq.) is dissolved in methanol (112 mL) at 50° C. A catalytic amount of p-toluenesulfonic acid (0.445 mg) is added, followed by trimethyl orthoformate (11.5 mL, 1.25 eq.). The mixture is allowed to react for 5 hours before methanol is allowed to distill off. Fresh methanol is added continuously to replace the distillate. When 100 mL of methanol have been distilled, the mixture is allowed to cool down to 25° C. in 1 hour. The suspension is further cooled down to 3° C. in 20 minutes, stirred at this temperature for 1 hour and filtered. The solid is washed with cold methanol and dried in vacuum for 15 hours (50° C., 50 mbar). Pure title compound is obtained as a light yellow powder (18.02 g, 80.8% yield).

후처리

  1. distillationto distill off
  2. additionFresh methanol is added continuously
  3. distillationWhen 100 mL of methanol have been distilled
  4. temperatureThe suspension is further cooled down to 3° C. in 20 minutes
  5. filtrationfiltered
  6. washThe solid is washed with cold methanol
  7. customdried in vacuum for 15 hours (50° C., 50 mbar)

출처 및 근거

ORD 기록
ord-a62330b7de104fd29ff657b06a63b8e2
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112673B2

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