Chloroacetyl chloride → N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-chloroacetamide

HRID 30796

반응식

HRID 30796 반응식
[CH3:1][NH:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>O1CCCC1>[CH3:1][NH:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:29](=[O:30])[CH2:28][Cl:27])[CH:9]=2)=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 597900164-(4-(Methylamino)-3-nitrophenoxy)pyridin-2-amine

생성물 1

HCID 59790002N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-chloroacetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-amine (1 eq) and triethylamine (2 eq) in tetrahydrofuran was treated with 2-chloroacetyl chloride and stirred for 15 minutes at room temperature. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuum to give crude product. Purification on silica gel with 2% methanol in methylene chloride gave N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-chloroacetamide as a bright orange solid. HPLC=3.82 min; MS: MH+=337.

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuum
  7. customto give crude product
  8. customPurification on silica gel with 2% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-5eeb8aad263b44a1bcb86954ad0d175e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423150B2

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