Phenyl isocyanate → n-{1-[(Anilinocarbonyl)amino]-2,2,2-trichloroethyl}-4-methylbenzamide

HRID 479495ノート

反応式

HRID 479495 の反応式
[NH2:1][CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]([Cl:6])([Cl:5])[Cl:4].[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[NH:23]([C:24]([NH:1][CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]([Cl:6])([Cl:4])[Cl:5])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 18770673N-(1-amino-2,2,2-trichloroethyl)-4-methylbenzamide

生成物 1

HCID 18770685n-{1-[(Anilinocarbonyl)amino]-2,2,2-trichloroethyl}-4-methylbenzamide収率 58%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of Example 38A (183 mg, 0.650 mmol) and phenyl isocyanate (77 mg, 0.65 mmol) in THF (4 mL) at ambient temperature was treated with triethylamine (0.93 mL, 0.66 mmol). The mixture was stirred for 10 hours, diluted with ethyl acetate (20 mL), and washed with aqueous NH4Cl (10 mL), water (10 mL), and brine (5 mL). The organic portion was dried (MgSO4), filtered, and concentrated to provide an oily residue which was purified by flash chromatography (elution with 5% methanol/CH2Cl2) to provide 151 mg of the desired product as an off-white solid.

後処理

  1. washwashed with aqueous NH4Cl (10 mL), water (10 mL), and brine (5 mL)
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide an oily residue which
  6. customwas purified by flash chromatography (elution with 5% methanol/CH2Cl2)

出典と根拠

ORDレコード
ord-3851b490f1514696b90e4924f1174f85
出典データセット
uspto-grants-2003_11
特許番号
US06645968B2

反応ノート

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