N-Methylisatoic anhydride → N-[3-(1H-Imidazol-1-yl)propyl]-2-(methylamino)benzamide

HRID 2164793Notes

Reaction equation

HRID 2164793 reaction equation
C[N:2]1[C:8](=O)[O:7][C:5](=O)[C:4]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:3]12.[N:14]1([CH2:19][CH2:20][CH2:21][NH2:22])[CH:18]=[CH:17][N:16]=[CH:15]1>O1CCOCC1>[CH3:8][NH:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([NH:22][CH2:21][CH2:20][CH2:19][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[O:7]

Participants

4

Reactant 2

HCID 25160N-Methylisatoic anhydrideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 13280097N-[3-(1H-Imidazol-1-yl)propyl]-2-(methylamino)benzamideYield 69.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Methylisatoic anhydride (17.7 g) was added in portions to a stirred solution of 3-imidazol-1-ylpropylamine (12.5 g) in dioxan (150 ml) over a period of 15 minutes. Stirring was continued for 40 minutes before the solution was evaporated in vacuo to give 2-methylamino-N-(3-imidazol-1-ylpropyl)benzamide (18.0 g), in the form of a buff coloured solid, m.p. 138°-141° C., after recrystallisation from isopropanol.

Workup

  1. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-908a83b5879847a88735022867ce69ea
Source dataset
uspto-grants-1985_03
Patent number
US04507315

Reaction notes

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