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

HRID 515324Notes

Reaction equation

HRID 515324 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-8687af6912874e2b8c73f7b33c2aea4b
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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