Sodium Hydroxide → 2-amino-5-chloro-N-(4-chlorophenyl)benzamide

HRID 844141

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HRID 844141 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[N+:17]([O-])=O)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH2:17])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 873788Benzamide, 5-chloro-N-(4-chlorophenyl)-2-nitro-

생성물 1

HCID 41860192-amino-5-chloro-N-(4-chlorophenyl)benzamide수율 97.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

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온도
70 °C

실험 절차

N-(4—Chlorophenyl)-5-chloro-2-nitrobenzamide (13.2 g, 42.4 mmol) and tin(II) chloride dihydrate (48 g, 213 mmol) were combined in ethyl acetate (90 mL) and the mixture was heated at 70° C. under a nitrogen atmosphere. After 15 minutes, the mixture was cooled to ambient temperature, then poured onto water (750 mL) and ethyl acetate (750 mL). The aqueous layer was adjusted to pH 8 with by addition of 1 N NaOH and a saturated NaHCO3 solution, and the layers were separated. The aqueous layer was further extracted with 500 mL of ethyl acetate. The combined organic extracts were washed with water (1 L), then brine (500 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 11.6 g (97% yield) of N-(4-chlorophenyl)-2-amino-5-chlorobenzamide as an off-white solid; NMR (CDCl3) 7.7 (br s, 1), 7.2-7.5 (m, 6), 6.7 (d, 1), 5.5 (br s, 2) ppm.

후처리

  1. temperaturethe mixture was cooled to ambient temperature
  2. customa saturated NaHCO3 solution, and the layers were separated
  3. extractionThe aqueous layer was further extracted with 500 mL of ethyl acetate
  4. washThe combined organic extracts were washed with water (1 L)
  5. dry with materialbrine (500 mL), dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-09f9fd8415eb4356aaf56ce84f5e2dd6
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380221B1

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