5-Chloroisatoic anhydride → 2-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide

HRID 2118648Notes

Reaction equation

HRID 2118648 reaction equation
[Cl:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9]C(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=O.[N:14]1([CH2:19][CH2:20][CH2:21][NH2:22])[CH:18]=[CH:17][N:16]=[CH:15]1>C(O)C>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=1[C:7]([NH:22][CH2:21][CH2:20][CH2:19][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[O:9]

Participants

4

Reactant 2

HCID 784805-Chloroisatoic anhydrideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 135889602-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.92 g of 5-chloroisatoic anhydride, 5.0 g of 1H-imidazole-1-propanamine and 75 ml of ethanol was stirred at room temperature for 20 hours and concentrated. The residue was washed onto a filter with ethanol, then washed with ether to give the desired product, mp 155°-157° C.

Workup

  1. concentrationconcentrated
  2. washThe residue was washed onto
  3. filtrationa filter with ethanol
  4. washwashed with ether

Sources & evidence

ORD record
ord-283a6fee03874373a246bff2582079a6
Source dataset
uspto-grants-1987_07
Patent number
US04680293

Reaction notes

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