2,3-Dichlorobenzoyl chloride → HCID 20242181, compound

HRID 1903560Notes

Reaction equation

HRID 1903560 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:13]1[C:14]([Cl:22])=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].[ClH:23].C1(C2N=CNC=2)C=CC=CC=1>O1CCCC1>[Cl:23][C:19]1[CH:20]=[CH:21][CH:13]=[C:14]([Cl:22])[C:15]=1[C:16]([N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1)=[O:17]

Participants

5

Reactant 3

HCID 179442,3-Dichlorobenzoyl chlorideHCID 178418822HCID 178418822, compoundHCID 178477959HCID 178477959, compound

Product 1

HCID 20242181HCID 20242181, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.88 g of 4-phenylimidazole are dissolved in 7 ml of tetrahydrofuran; a solution of 2.12 g of dichlorobenzoyl chloride in 5 ml of tetrahydrofuran is then added, and the mixture is heated, in the course of which 4-phenylimidazole hydrochloride precipitates. The mixture is diluted with 15 ml of tetrahydrofuran, and is filtered at room temperature in vacuo. The filtrate is subsequently evaporated to dryness in a rotary evaporator, and the residue is recrystallised from 15 ml of ethyl acetate. The yield is 1.55 g (48.9% of theory) of the desired product, m.p. 135°-136° C. By concentration of the mother liquor by evaporation and recrystallisation from 8 ml of benzene, there are obtained a further two fractions (0.76 g, m.p. 135°-136° C.; and 0.41 g, m.p. 134°-135° C.). The total yield is hence 2.72 g (85.8% of theory).

Workup

  1. customprecipitates
  2. additionThe mixture is diluted with 15 ml of tetrahydrofuran
  3. filtrationis filtered at room temperature in vacuo
  4. customThe filtrate is subsequently evaporated to dryness in a rotary evaporator
  5. customthe residue is recrystallised from 15 ml of ethyl acetate
  6. customBy concentration of the mother liquor by evaporation and recrystallisation from 8 ml of benzene, there
  7. customare obtained a further two fractions (0.76 g, m.p. 135°-136° C.; and 0.41 g, m.p. 134°-135° C.)
  8. customThe total yield

Sources & evidence

ORD record
ord-0cb65022f236453cbf8d1e2f1ba20e69
Source dataset
uspto-grants-1984_03
Patent number
US04436892

Reaction notes

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