Triethylamine → HCID 20188428, compound

HRID 1903561Notes

Reaction equation

HRID 1903561 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[C:21]=1[C:22](Cl)=[O:23]>O1CCCC1>[Cl:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[C:21]=1[C:22]([N:11]1[CH:10]=[CH:9][N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 695912-PhenylimidazoleHCID 22596843HCID 22596843, compound

Product 1

HCID 20188428HCID 20188428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

13.4 g of 2-phenylimidazole are dissolved in 120 ml of tetrahydrofuran; 9.7 g of triethylamine are added, and there are then added dropwise, at reflux temperature within 10 minutes, 20.5 g of 2-chloro-6-nitro-benzoyl chloride, dissolved in 40 ml of tetrahydrofuran. The mixture is refluxed for 1 hour, and the precipitated triethylamine hydrochloride is removed at room temperature by filtration in vacuo. After removal of the solvent in the rotary evaporator, the crude product is recrystallised from 65 ml of acetonitrile. The yield is 25.1 g (82.4% of theory) of product, m.p. 147°-148° C. Concentration of the mother liquor by evaporation produces a further 2.1 g (6.9% of theory) of this product, m.p. 144°-147° C.

Workup

  1. additionthere are then added dropwise
  2. temperatureat reflux temperature within 10 minutes
  3. temperatureThe mixture is refluxed for 1 hour
  4. customthe precipitated triethylamine hydrochloride is removed at room temperature by filtration in vacuo
  5. customAfter removal of the solvent
  6. customin the rotary evaporator
  7. customthe crude product is recrystallised from 65 ml of acetonitrile
  8. customConcentration of the mother liquor by evaporation
  9. customproduces a further 2.1 g (6.9% of theory) of this product, m.p. 144°-147° C.

Sources & evidence

ORD record
ord-fb6ce386826f44489b9df37f358b2003
Source dataset
uspto-grants-1984_03
Patent number
US04436892

Reaction notes

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