Chloranil → beta-Alanine Benzyl Amine Urea

HRID 1444679Notes

Reaction equation

HRID 1444679 reaction equation
Cl.[CH2:2]([NH:9][C:10](=[O:14])[CH2:11][CH2:12][NH2:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC(Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl.[N-:27]=C=O.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>CN1CCOCC1>[NH2:9][C:10]([NH2:27])=[O:14].[CH2:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:13][CH2:12][CH2:11][C:10]([OH:14])=[O:18]

Participants

6

Reactant 4

HCID 8371ChloranilHCID 94429TriphosgeneHCID 105034IsocyanateHCID 510519593-amino-N-benzylpropanamide hydrochloride

Product 1

HCID 86761057beta-Alanine Benzyl Amine Urea

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

To a solution of β-alanine benzyl amide HCl (80 mg, 0.36 mmol) in N-methyl morpholine (120 μi) and MC (2 mL), triphosgene (0.72 mmol) was added at room temperature. After 10 minutes, the resulted isocyanate solution was added to a suspension of the secondary amine resin obtained in above step (2) (100 mg, 0.048 mmol) and kept shaking for 3 hrs at room temperature. The resin was washed with DMF, MeOH and MC, and the completion of reaction was checked with chloranil test.

Workup

  1. customobtained in above step (2) (100 mg, 0.048 mmol)
  2. washThe resin was washed with DMF, MeOH and MC
  3. customthe completion of reaction

Sources & evidence

ORD record
ord-a07d1917111d4a6bb2b539df5f0d37ed
Source dataset
uspto-grants-2010_02
Patent number
US07662960B2

Reaction notes

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