Cyclobutylamine → Ethyl 4-(3-cyclobutylureido)benzoate

HRID 1878376Notes

Reaction equation

HRID 1878376 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[N:6]([C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1)=[C:7]=[O:8]>ClCCl>[CH:1]1([NH:5][C:7](=[O:8])[NH:6][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 4353410Ethyl 4-(3-cyclobutylureido)benzoateYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclobutylamine (27.91 g, 392.4 mmol, 33.5 mL) was added dropwise to a stirred solution of ethyl 4-isocyanatobenzoate (25 g, 130.8 mmol) in dichloromethane. After 40 minutes stirring, the solid precipitate that had formed was filtered off and dried to afford the title compound (30.28 g). MS (ESI) m/z 263.1 [M+H]+

Workup

  1. customthe solid precipitate that had formed
  2. filtrationwas filtered off
  3. customdried

Sources & evidence

ORD record
ord-674a9c16d3984421b1780dd87c52f72a
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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