Benzylamine → (2-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl ester

HRID 639630ノート

反応式

HRID 639630 の反応式
[CH2:1]([O:3][C:4](=[O:20])[NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8](Cl)[C:7]=1[N+:17]([O-:19])=[O:18])[CH3:2].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:3][C:4](=[O:20])[NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]=1[N+:17]([O-:19])=[O:18])[CH3:2]

参加物

5

反応物 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 86614475(2-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl ester

生成物 1

HCID 67456211(2-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl ester収率 87.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

(2-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl ester (300 mg, 0.96 mmol) was dissolved in 10 mL of tetrahydrofuran and benzylamine (0.103 mL, 0.96 mmol) was added followed by triethylamine (0.194 mL, 1.91 mmol) and the reaction mixture was stirred at 60° C. overnight. The solvent was removed and the solid was partitioned in ethyl acetate/water (50 mL/30 mL), the organic layer was dried over MgSO4, concentrated and purified by column chromatography on silica eluting with a gradient of 0% to 10% of methanol in ethyl acetate in to give 323 mg of the title compound as a yellow solid.

後処理

  1. customThe solvent was removed
  2. customthe solid was partitioned in ethyl acetate/water (50 mL/30 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica eluting with a gradient of 0% to 10% of methanol in ethyl acetate in

出典と根拠

ORDレコード
ord-66e78054c4504ec3ba45af3c2a068e48
出典データセット
uspto-grants-2010_04
特許番号
US07691877B2

反応ノート

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