Cyclopropanemethanamine → Ethyl 4-(3-(cyclopropylmethyl)ureido)benzoate

HRID 408861Notes

Reaction equation

HRID 408861 reaction equation
[CH:1]1([CH2:4][NH2:5])[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([CH2:4][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)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 3830959Ethyl 4-(3-(cyclopropylmethyl)ureido)benzoateYield 107.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To cyclopropylmethanamine (57.5 mmol, 4.99 ml, 4.09 g) in dichloromethane (40 mL) was added to ethyl 4-isocyanatobenzoate (52.3 mmol, 10 g) in dichloromethane (45 mL) and the reaction stirred overnight. The reaction was then concentrated under reduced pressure to give the title compound (14.7 g).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-a025eb4f1c524d379e0511ca45ef8992
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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