Cyclobutylamine → Ethyl 4-(3-cyclobutylureido)benzoate

HRID 408845Notes

Reaction equation

HRID 408845 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-3caceeb1eeb54af28b9756eaa35284e6
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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