Sodium Hydroxide → N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

HRID 50004

Reaktionsgleichung

Reaktionsgleichung von HRID 50004
[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=O)[C:4]=1[CH3:12])=[O:2].O[C:14]1C2N=NNC=2C=C[CH:15]=1.C([NH:25][CH2:26][CH2:27][NH:28][CH2:29][CH3:30])C.[OH-].[Na+]>O.[Cl-].[Na+].O.C(=O)(O)[O-].[Na+].C(N(CC)CC)C.CN(C)C=O>[CH2:14]([N:28]([CH2:29][CH3:30])[CH2:27][CH2:26][NH:25][C:9]([C:5]1[C:4]([CH3:12])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=1[CH3:8])=[O:11])[CH3:15]

Komponenten

10

Edukt 4

HCID 14798Sodium HydroxideHCID 67105N,N'-DiethylethylenediamineHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic AcidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 20761785N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 3000 mL of water, 2000 mL of brine and 3000 mL of saturated sodium bicarbonate solution and the pH adjusted to greater than 10 with 10 N sodium hydroxide. The mixture was extracted twice with 5000 mL each time of 10% methanol in dichloromethane and the extracts combined, dried over anhydrous magnesium sulfate and rotary evaporated to dryness. The mixture was with diluted with 1950 mL of toluene and rotary evaporated again to dryness. The residue was triturated with 3:1 hexane:diethyl ether (4000 mL). The solids were collected by vacuum filtration, washed twice with 400 mL of ethyl acetate and dried under vacuum at 34° C. for 21 hours to give 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (819 g, 43% yield) as a light brown solid. 1H-NMR (dimethylsulfoxide-d6) δ0.96 (t, 6H, 2×CH3), 2.31, 2.38 (2×s, 2×CH3), 2.51 (m, 6H 3×CH2), 3.28 (m, 2H, CH2), 7.34 (m, 1H, amide NH), 9.56 (s, 1H, CHO), 11.86 (s, 1H, pyrrole NH). MS m/z 266 [M+1].

Aufarbeitung

  1. additionwere added
  2. extractionThe mixture was extracted twice with 5000 mL each time of 10% methanol in dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customrotary evaporated to dryness
  5. additionwith diluted with 1950 mL of toluene
  6. customrotary evaporated again to dryness
  7. customThe residue was triturated with 3:1 hexane
  8. filtrationThe solids were collected by vacuum filtration
  9. washwashed twice with 400 mL of ethyl acetate
  10. customdried under vacuum at 34° C. for 21 hours

Quellen und Nachweise

ORD-Eintrag
ord-4280e8a1072d4ca989f211bca84eef5e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710067B2

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