2-Chloro-N-(propylcarbamoyl)acetamide → HCID 59202067, compound

HRID 1685618Notes

Reaction equation

HRID 1685618 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].Cl[CH2:11][C:12]([NH:14][C:15]([NH:17][CH2:18][CH2:19][CH3:20])=[O:16])=[O:13].C(=O)([O-])O.[Cs+]>CN1C(=O)CCC1>[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:11][C:12](=[O:13])[NH:14][C:15]([NH:17][CH2:18][CH2:19][CH3:20])=[O:16])=[O:5]

Participants

5

Reactant 3

HCID 24473492-Chloro-N-(propylcarbamoyl)acetamideHCID 2734983Cesium bicarbonateHCID 5369209Monomethyl Fumarate

Product 1

HCID 59202067HCID 59202067, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, methyl hydrogen fumarate (MHF) (0.50 g, 3.84 mmol) dissolved in NMP was reacted at ca. 55° C. with 1-(2-chloroacetyl)-3-propyl urea (0.82 g, 4.60 mmol) in the presence of CsHCO3 (0.89 g, 4.61 mmol) to provide 0.02 g (2% yield) of the title compound (19) as a white solid. Addition of methanol (MeOH) afforded 0.49 g (48% yield) of white solid. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.99 (m, 2H), 4.77 (s, 2H), 3.82 (s, 3H), 3.25-3.24 (q, 2H, J=5.6 Hz), 1.57-1.55 (q, 2H, J=7.2 Hz), 0.95-0.91 (t, 3H, J=7.6 Hz). MS (ESI): m/z 273.08 (M+H)+.

Sources & evidence

ORD record
ord-379c61d5cbb94fe2904b47b5fe0ded1f
Source dataset
uspto-grants-2012_04
Patent number
US08148414B2

Reaction notes

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