Phenyl isocyanate → tert-butyl 3-methyl4-(N'-phenylureido)phenylacetate

HRID 354350Notes

Reaction equation

HRID 354350 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:16].CCN(CC)CC.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH3:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:31]([NH:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:32]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512058tert-butyl 3-methyl4-(N'-phenylureido)phenylacetateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-3-methylphenylacetate (1.20 g, 5.42 mmol) and Et3N (830 ml, 5.95 mmol) in THF (10 ml) was added phenyl isocyanate (650 ml, 5.98 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to a small volume and diluted with n-hexane. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give tert-butyl 3-methyl-4-(N′-phenylureido)phenylacetate (1.12 g, 61%) as a white crystalline powder. mp 143-145° C; 1H-NMR (CDCl3) δ1.47 (s, 9 H), 2.09 (s, 3 H), 3.47 (s, 2 H), 6.44 (s, 1H), 7.01-7.07 (m, 4 H), 7.16-7.27 (m, 2 H), 7.30-7.33 (m, 2 H), 7.45-7.47 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additiondiluted with n-hexane
  3. customResulting precipitate
  4. customwas collected under a reduced pressure
  5. washthe filtrate was washed with n-hexane

Sources & evidence

ORD record
ord-4e4c463197a6463f9e2193deb30fb3f6
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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