Hydrochloric Acid → 1-Phenylisatin

HRID 751325

반응식

HRID 751325 반응식
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)(=[O:18])[C:15](Cl)=[O:16].Cl>C1(C)C=CC=CC=1>[C:8]1([N:7]2[C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15](=[O:16])[C:14]2=[O:18])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11487DiphenylamineHCID 65578Oxalyl chloride

생성물 1

HCID 128841-Phenylisatin수율 94.2%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
60 °C

실험 절차

The title compound is prepared following the procedures of Bryant, N. M., III et al. Syn Commun, 23, 1617-25 (1993) as follows. A solution of diphenylamine (26.6 g, 157 mmol) in toluene (65 mL) is added slowly to a solution of oxalyl chloride (14.8 mL, 170 mmol) in toluene (35 mL) while cooling in an ice-water bath to maintain the temperature below 40° C. The resulting brown slurry is heated at 55-65° C. for 1 hr. CAUTION: There is vigorous evolution of hydrogen chloride gas. Approximately 100 mL of solvent is removed by distillation (it contains unreacted oxalyl chloride) and the residue is heated overnight at 118-125° C. The reaction is cooled and then poured into ice-water (200 mL), extracted with ethyl acetate (4×250 mL). The combined extract is dried, filtered and concentrated to give 1-phenyl-1H-indole-2,3-dione (33.0 g, 94% yield). H-NMR 7.70 (1H, d), 7.58 (3H, d), 7.43 (3H, m), 7.19 (1H, t), 6.90 (1H, d).

후처리

  1. customThe title compound is prepared
  2. temperaturewhile cooling in an ice-water bath
  3. temperatureto maintain the temperature below 40° C
  4. customApproximately 100 mL of solvent is removed by distillation (it contains unreacted oxalyl chloride)
  5. temperaturethe residue is heated overnight at 118-125° C
  6. temperatureThe reaction is cooled
  7. additionpoured into ice-water (200 mL)
  8. extractionextracted with ethyl acetate (4×250 mL)
  9. extractionThe combined extract
  10. customis dried
  11. filtrationfiltered
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8302e2292c144021aaaa9285f5638f1b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405300B2

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