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

HRID 1807707Notes

Reaction equation

HRID 1807707 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-874251e8ba324526a3cbd46f7f0217f8
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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