Toluene → HCID 21312573, compound

HRID 971922Notes

Reaction equation

HRID 971922 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7][C:8](=[O:11])[N:9]=2)[C:5]([Br:12])=[C:4]([Br:13])[C:3]=1[Br:14].[C:15]1([CH3:21])[CH:20]=[CH:19]C=CC=1.[C:22](=O)([O-])[O-:23].[K+].[K+].Cl[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].CN(C)C=[O:39]>>[CH3:35][O:34][C:32]([CH2:31][CH2:30][CH2:29][N:9]1[C:10]2[C:2]([Br:1])=[C:3]([Br:14])[C:4]([Br:13])=[C:5]([Br:12])[C:6]=2[N:7]([CH2:21][CH2:15][CH2:20][C:19]([O:23][CH3:22])=[O:39])[C:8]1=[O:11])=[O:33]

Participants

6

Reactant 5

HCID 1140Toluene2×HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 16750062HCID 16750062, compound

Product 1

HCID 21312573HCID 21312573, compound

Procedure

45.48 g (0.1 mol) of 4,5,6,7-tetrabromobenzimidazolone are suspended in 250 ml of dimethylformamide and 75 ml of toluene and 27.4 g (0.2 mol) of finely powdered, dry potassium carbonate are added. 30.07 g (0.22 mol) of methyl γ-chlorobutyrate are added to this suspension and the mixture is heated up to the reflux temperature (internal temperature 108°-120° C.), whilst stirring. The toluene serves to remove water azeotropically. After 25 hours, the mixture is cooled to 80°-85° C. and filtered whilst still hot. The solution is concentrated to dryness and the desired product is isolated in the form of colourless crystals. Yield: 58.35 g (89.1% of theory).

Workup

  1. temperaturethe mixture is heated up to the reflux temperature (internal temperature 108°-120° C.)
  2. customto remove water azeotropically
  3. temperaturethe mixture is cooled to 80°-85° C.
  4. filtrationfiltered whilst still hot
  5. concentrationThe solution is concentrated to dryness

Sources & evidence

ORD record
ord-2735321b32314b9cb1516ddbde53fec9
Source dataset
uspto-grants-1979_07
Patent number
US04161603

Reaction notes

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