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

HRID 30796

反応式

HRID 30796 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5eeb8aad263b44a1bcb86954ad0d175e
出典データセット
uspto-grants-2008_09
特許番号
US07423150B2

関連ノート

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