Triethylamine → HCID 20242183, compound

HRID 1903559Notes

Reaction equation

HRID 1903559 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]([Cl:26])[C:18]=1[C:19](Cl)=[O:20]>O1CCCC1>[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[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

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 178437635HCID 178437635, compound

Product 1

HCID 20242183HCID 20242183, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

22.02 g of 2-ethyl-4-methyl-imidazole and 20.85 g of triethylamine are dissolved in 250 ml of tetrahydrofuran. There are then added dropwise, at reflux temperature within 20 minutes, 41.88 g of 2,6-dichlorobenzoyl chloride, dissolved in 100 ml of tetrahydrofuran, and the mixture is refluxed for 30 minutes, and subsequently further processed as described in Example 1. Recrystallisation of the crude product from 120 ml of acetonitrile yields 36.4 g of product (64.3% of theory), m.p. 112°-113.5° C.

Workup

  1. additionThere are then added dropwise
  2. temperatureat reflux temperature within 20 minutes
  3. temperaturethe mixture is refluxed for 30 minutes
  4. customRecrystallisation of the crude product from 120 ml of acetonitrile

Sources & evidence

ORD record
ord-3a291cf7474d4e51bed0d6ce2136eff4
Source dataset
uspto-grants-1984_03
Patent number
US04436892

Reaction notes

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