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

HRID 479495노트

반응식

HRID 479495 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3851b490f1514696b90e4924f1174f85
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645968B2

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