Hydrochloric Acid → HCID 67722372, compound

HRID 256590Notes

Reaction equation

HRID 256590 reaction equation
C(O[C:9](=[O:32])[CH:10]([N:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](=[O:31])C(Cl)(Cl)Cl)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])C1C=CC=CC=1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:37][NH2:38].C(N(CC)CC)C.Cl>CN(C)C=O>[CH2:14]([O:13][C:11]([CH:10]1[N:21]2[CH:25]=[CH:24][CH:23]=[C:22]2[C:26](=[O:31])[N:38]([CH2:37][C:36]2[CH:39]=[CH:40][C:41]([Cl:42])=[C:34]([Cl:33])[CH:35]=2)[C:9]1=[O:32])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1608Benzenemethanamine, 3,4-dichloro-HCID 8471TriethylamineHCID 54262702HCID 54262702, compound

Product 1

HCID 67722372HCID 67722372, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(2-trichloroacetylpyrrol-1-yl)malonic acid dibenzyl ester (30.0 g), 3,4 dichlorobenzylamine (11.7 g) and triethylamine (18.4 g, 25.0 ml) in anhydrous dimethylformamide (70 ml) was stirred under the stream of nitrogen at 70° C. for 2 hours. After cooling, the reaction mixture was poured into 5% hydrochloric acid and extracted with ethyl acetate. The extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel using n-hexane/ethyl acetate (3:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (16.0 g, 59.5%) as colorless crystals, mp 104°-106° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. additionFractions containing the title compound
  7. customevaporated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-40793ff04fc54c20ab16cfe546988122
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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