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

HRID 479495Notes

Reaction equation

HRID 479495 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3851b490f1514696b90e4924f1174f85
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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