Triethylamine → HCID 20467443, compound

HRID 1903562Notes

Reaction equation

HRID 1903562 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[C:6]([CH3:8])[N:7]=1)[CH3:2].C(N(CC)CC)C.[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:18]=1[C:19](Cl)=[O:20]>O1CCCC1.Cl.C(N(CC)CC)C>[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:18]=1[C:19]([N:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:3]1[CH2:1][CH3:2])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22596843HCID 22596843, compoundHCID 178437635HCID 178437635, compound

Product 1

HCID 20467443HCID 20467443, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 11130Triethylamine hydrochlorideSolvent

Procedure

15.4 g of 2-ethyl-4-methyl-imidazole are dissolved in 100 ml of tetrahydrofuran; 14.6 g of triethylamine are added, and there can then added dropwise, within 30 minutes at reflux temperature, 30.8 g of 2-chloro-6-nitrobenzoyl chloride, dissolved in 50 ml of tetrahydrofuran, in the process of which triethylamine hydrochloride precipitates. After 3 hours of refluxing, the mixture is filtered with suction, and the solvent is removed in the rotary evaporator. Recrystallisation of the residue from 85 ml of toluene yields 27.7 g (67.3% of theory) of the desired product, m.p. 119°-120° C.

Workup

  1. additionthere can then added dropwise, within 30 minutes
  2. customprecipitates
  3. temperatureAfter 3 hours of refluxing
  4. filtrationthe mixture is filtered with suction
  5. customthe solvent is removed in the rotary evaporator
  6. customRecrystallisation of the residue from 85 ml of toluene

Sources & evidence

ORD record
ord-9a2acad788a645d38dc13b894e906a3e
Source dataset
uspto-grants-1984_03
Patent number
US04436892

Reaction notes

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