Hydrochloric Acid → N-(2,6-dichloro-4-cyanophenyl)acetamide

HRID 1819675

반응식

HRID 1819675 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[NH2:10])[C:5]#[N:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:22](Cl)(=[O:24])[CH3:23].Cl>C1COCC1.O.C(Cl)Cl>[C:22]([NH:10][C:9]1[C:2]([Cl:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=1[Cl:11])(=[O:24])[CH3:23]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 5227064-Amino-3,5-dichlorobenzonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

HCID 2735977N-(2,6-dichloro-4-cyanophenyl)acetamide

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Step B (1): To a solution of 3,5-dichloro-4-amino-benzonitrile (187 mg, 1 mmol) in 4 mL of THF at room temperature was added 2.2 mL of 1.0 M NaHMDS in THF. The resulting reaction mixture was stirred at room temperature for 30 min, at which time acetyl chloride (3.1 mmol) was added. DCM (100 mL) and water (100 mL) were added to the reaction mixture after being stirred overnight, followed by the addition of 5 mL of a 1.4 N HCl aqueous solution. The layers were separated and the aqueous layer was extracted with DCM (2×100 mL). The extracts were combined and solvents were evaporated in vacuo. The residue was purified by HPLC to give 4-acetamido-3,5-dichloro-benzonitrile. MS (ESI) (M−H)+=227.05. 1H-NMR (300 MHz, CDCl3) δ 7.63 (s, 2 H), 2.21 (s, 3 H).

후처리

  1. customThe resulting reaction mixture
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×100 mL)
  5. customsolvents were evaporated in vacuo
  6. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-26fe6ec0bd5b4872ba768de4f425f61c
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601751B2

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