4-Bromo-2-chloroaniline → 4-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid

HRID 494698

반응식

HRID 494698 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([Cl:19])[CH:13]=1.Cl[C:21]1[C:26]([C:27]([OH:29])=[O:28])=[CH:25][N:24]=[C:23]([Cl:30])[C:22]=1[Cl:31]>C1COCC1.Cl.C(OCC)(=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:21]2[C:26]([C:27]([OH:29])=[O:28])=[CH:25][N:24]=[C:23]([Cl:30])[C:22]=2[Cl:31])=[C:14]([Cl:19])[CH:13]=1

참가 물질

7

반응물 3

HCID 6101694-Bromo-2-chloroanilineHCID 2733832Lithium HexamethyldisilazideHCID 115866384,5,6-TRICHLORONICOTINIC ACID

생성물 1

HCID 116612174-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid수율 75%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

LiHMDS (1.0 M solution in hexanes, 53.0 mL, 53.0 mmol) was added dropwise to a stirred solution of 4-bromo-2-chlorophenylamine (7.10 g, 35.0 mmol) in THF (15 mL) cooled to −78° C. After one hour, 4,5,6-trichloronicotinic acid (3.73 g, 16.5 mmol) was added dropwise as a solution in THF (12 mL). The reaction was allowed to warm to room temperature slowly while stirring overnight. The suspension was diluted with 1 M HCl and ethyl acetate, and the aqueous phase was extracted with ethyl acetate (3×). The combined organic phases were dried over Na2SO4 and concentrated to a tan solid. The solid was triturated with diethyl ether overnight and the solids were isolated by filtration to provide the desired product (25) as a tan-colored solid (4.85 g, 75%). MS APCI (−) m/z 395, 397 (M-, Cl, Br pattern) detected.

후처리

  1. temperatureto warm to room temperature slowly
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated to a tan solid
  5. customThe solid was triturated with diethyl ether overnight
  6. customthe solids were isolated by filtration

출처 및 근거

ORD 기록
ord-c749a76de9364a98aea48b8889080e4f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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