2-(1H-benzimidazol-2-yl)isoindole-1,3-dione → N-(benzimidazol-2-yl)-2-(n-butoxycarbonyl)-benzamide

HRID 596574

Reaction equation

HRID 596574 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20]>C(O)CCC>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[NH:10][C:14](=[O:15])[C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=1[C:11]([O:15][CH2:14][CH2:13][CH2:12][CH3:11])=[O:20]

Participants

3

Reactant 1

HCID 27557042-(1H-benzimidazol-2-yl)isoindole-1,3-dione

Product 1

HCID 21449938N-(benzimidazol-2-yl)-2-(n-butoxycarbonyl)-benzamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-(Benzimidazol-2-yl)phthalimide (4 g.) in 200 ml. of n-butyl alcohol is heated at 115° C. for 35 minutes. On cooling, colorless needles form. These are removed by suction filtration, washed with butyl alcohol and finally with diethyl ether. After drying for three hours at 125° C. under vacuum, a yield of 2.5 g. of N-(benzimidazol-2-yl)-2-(n-butoxycarbonyl)-benzamide, m.p. 187° C., is obtained. Additional heating to higher temperatures causes a reclosure to the phthalimide and remelting which corresponds to the phthalimide, m.p. 267°-268° C.

Workup

  1. temperatureOn cooling
  2. customcolorless needles form
  3. customThese are removed by suction filtration
  4. washwashed with butyl alcohol and finally with diethyl ether
  5. customAfter drying for three hours at 125° C. under vacuum

Sources & evidence

ORD record
ord-95940ae3f397417aa28f55ef2a7ccea5
Source dataset
uspto-grants-1977_03
Patent number
US04011236

Linked notes

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